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

HRID 21980

反応式

HRID 21980 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6386tert-Butanol溶媒

反応条件

温度
55 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-5fdd0e3dd94345ac930309f298b22ccd
出典データセット
uspto-grants-1995_06
特許番号
US05426103

関連ノート

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