Lithium borohydride → (R)-2,2-Dimethyl-3-(1-oxoheptyl)-4-oxazolidinemethanol

HRID 1450741ノート

反応式

HRID 1450741 の反応式
C[O:2][C:3]([C@@H:5]1[CH2:9][O:8][C:7]([CH3:11])([CH3:10])[N:6]1[C:12](=[O:19])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=O.[BH4-].[Li+]>CCOCC>[CH3:11][C:7]1([CH3:10])[N:6]([C:12](=[O:19])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[C@H:5]([CH2:3][OH:2])[CH2:9][O:8]1

参加物

4

反応物 2

HCID 4148881Lithium borohydrideHCID 53934458(S)-2,2-Dimethyl-3-(1-oxoheptyl)-4-oxazolidinecarboxylic Acid Methyl Ester

生成物 1

HCID 54137581(R)-2,2-Dimethyl-3-(1-oxoheptyl)-4-oxazolidinemethanol

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

実験手順

A solution of 8a (296 mg, 1.09 mmol) in dry ether (1 mL) is treated with lithium borohydride (2M solution in THF, 0.55 mL, 1.09 meq) under an argon atmosphere. The mixture is stirred for 3 h at reflux and 18 h at room temperature. The resulting mixture is diluted with ether and quenched with methanol. The volatiles are removed and the residue is taken up in EtOAc/H2O. Workup provides the crude alcohol which is purified by chromatography (2:1 hexane/EtOAc): NMR δ0.88 (m, 3H), 1.30 (m, 6H), 1.54 (s, 3H), 1.62 (s, 3H), 2.35 (m, 2H), 3.30-4.40 (complex m, 6H); MS (HR-E1) m/z 243.1837 (M calcd. for C13H25NO3 243.1840); [α]D26 =-5±1 (CHCl3).

後処理

  1. customquenched with methanol
  2. customThe volatiles are removed

出典と根拠

ORDレコード
ord-66daa9755dae42ffaefc422a20dd1a7a
出典データセット
uspto-grants-1997_02
特許番号
US05602275

反応ノート

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