Methanol → 3-t-Butoxycarbonylmethyl-10-hydroxymethyl-2-oxo-1-azacyclodecane

HRID 5407

반응식

HRID 5407 반응식
[C:1]([O:5][C:6]([CH2:8][CH:9]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH:12]([C:19](OCC)=[O:20])[NH:11][C:10]1=[O:24])=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].CO>C(O)(C)(C)C>[C:1]([O:5][C:6]([CH2:8][CH:9]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH:12]([CH2:19][OH:20])[NH:11][C:10]1=[O:24])=[O:7])([CH3:2])([CH3:4])[CH3:3]

참가 물질

5

반응물 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 19930811Ethyl 3-t-butoxycarbonylmethyl-2-oxo-1-azacyclodecane-10-carboxylate

생성물 1

HCID 199308433-t-Butoxycarbonylmethyl-10-hydroxymethyl-2-oxo-1-azacyclodecane

시약·촉매·용매 1

HCID 6386tert-Butanol용매

반응 조건

온도
55 °C

실험 절차

The major isomer of ethyl 3-t-butoxycarbonylmethyl-2-oxo-1-azacyclodecane-10-carboxylate (0.68 g, 2.0 mmol) is dissolved in t-butanol (10 mL). Sodium borohydride (0.23 g, 6.0 mmol) is added and the reaction is warmed to 55° C. Methanol (2.0 mL) is added over a twenty minute period, and the reaction is kept at 55° C. for an additional 1 hour. The reaction is then partitioned between ethyl acetate and water, and the aqueous phase is extracted several times with ethyl acetate. The combined organic layers are dried (MgSO4), and the solvent is evaporated. The crude product is purified by silica gel chromatography (50% ethyl acetate/hexane) to give 3-t-butoxycarbonylmethyl-10-hydroxymethyl-2-oxo-1-azacyclodecane, MS: M+1=300.

후처리

  1. customThe reaction is then partitioned between ethyl acetate and water
  2. extractionthe aqueous phase is extracted several times with ethyl acetate
  3. dry with materialThe combined organic layers are dried (MgSO4)
  4. customthe solvent is evaporated
  5. customThe crude product is purified by silica gel chromatography (50% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-429516784f194c80be8e088df5ef86d4
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05244889

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