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【结 构 式】

【分子编号】65467

【品名】(1S,4R)-4-[(N,N-di-Boc)amino]-2-cyclopentenol

【CA登记号】 

【 分 子 式 】C15H25NO5

【 分 子 量 】299.36724

【元素组成】C 60.18% H 8.42% N 4.68% O 26.72%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(XXXI)

The preparation of the cyclopentylamino intermediates (I) and (XIX) is shown in Scheme 4. Reaction of (1S,4R)-4-acetoxy-2-cyclopentenol (XXX) with di-tert-butyl iminodicarboxylate in the presence of NaH and Pd(PPh3)4 produces the di-Boc-protected aminocyclopentenol (XXXI), which undergoes dihydroxylation to triol (XXXII) by means of N-methylmorpholine N-oxide and a catalytic amount of osmium tetroxide. After acidic deprotection of the di-Boc derivative (XXXII), the resulting amino triol (XXXIII) is converted to the key acetonide (I) upon heating with 2,2-dimethoxypropane and catalytic HCl in acetone (1, 2). The O-hydroxyethyl derivative (XIX) is prepared by protection of aminoalcohol (I) as the benzyl carbamate (XXXIV), followed by O-alkylation with ethyl bromoacetate and potassium tert-butoxide to give (XXXV). Subsequent reduction of ester (XXXV) with LiBH4 in THF furnishes the corresponding hydroxyethyl derivative (XXXVI), from which the N-(benzyloxycarbonyl) group is removed by catalytic hydrogenation over Pd/C (3). Scheme 4.

1 Guile, S., Hardern, D., Willis, P., Springthorpe, B., Ingall, A. (AstraZeneca AB; AstraZeneca plc). Novel triazolo(4,5-d)pyrimidine compounds. EP 1135391, JP 2002531567, JP 2007084551, US 2003144305, US 2006025590, US 6525060, WO 0034283.
2 Bohlin, M., Lassen, B., Cosgrove, S. (AstraZeneca AB). New crystalline and amorphous form of triazolo(4,5-d)pyrimidine compound. CA 2408596, EP 1289992, EP 1493745, JP 2003535092, US 2003181469, US 2007173518, WO 0192262.
3 Larsson, U., Magnusson, M., Musil, T., Palmgren, A. (AstraZeneca AB). Triazolo pyrimidine compounds. CA 2408914, EP 1299390, JP 2003535093, US 2003148888, US 2006041132, US 2007049755, US 7067663, WO 0192263.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 65443 (3aR,4S,6R,6aS)-6-Aminotetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-ol; (3aS,4R,6S,6aR)-6-Hydroxy-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-amine 155899-66-4 C8H15NO3 详情 详情
(XIX) 65458 2-[[(3aR,4S,6R,6aS)-6-Aminotetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol 274693-55-9 C10H19NO4 详情 详情
(XXX) 45407 (1R,4S)-4-hydroxy-2-cyclopenten-1-yl acetate; (1S,4R)-4-acetoxy-2-cyclopentenol 60410-16-4 C7H10O3 详情 详情
(XXXI) 65467 (1S,4R)-4-[(N,N-di-Boc)amino]-2-cyclopentenol   C15H25NO5 详情 详情
(XXXII) 65468     C15H27NO7 详情 详情
(XXXIII) 65469     C5H11NO3.HCl 详情 详情
(XXXIV) 65470 N-[(3aS,4R,6S,6aR)-Tetrahydro-6-hydroxy-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]carbamicacid phenylmethyl ester 274693-53-7 C16H21NO5 详情 详情
(XXXV) 65471     C20H27NO7 详情 详情
(XXXVI) 65472 N-[(3aS,4R,6S,6aR)-Tetrahydro-6-(2-hydroxyethoxy)-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]carbamic acid phenylmethyl ester 274693-54-8 C18H25NO6 详情 详情
Extended Information