Lithium Hydroxide → (2S,3R)-1-[(tert-Butoxy)carbonyl]-3-methoxypyrrolidine-2-carboxylic acid

HRID 1527322ノート

反応式

HRID 1527322 の反応式
C[O:2][C:3]([C@@H:5]1[C@H:9]([O:10][CH3:11])[CH2:8][CH2:7][N:6]1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[O:4].[Li+].[OH-]>C1COCC1.O>[C:15]([O:14][C:12]([N:6]1[CH2:7][CH2:8][C@@H:9]([O:10][CH3:11])[C@H:5]1[C:3]([OH:4])=[O:2])=[O:13])([CH3:18])([CH3:16])[CH3:17]

参加物

5

反応物 2

HCID 3939Lithium Hydroxide2 回HCID 66619640N-BOC-3(R)-methoxy-(L)-proline, methyl ester

生成物 1

HCID 69351760(2S,3R)-1-[(tert-Butoxy)carbonyl]-3-methoxypyrrolidine-2-carboxylic acid

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of (2S,3R)-3-methoxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (150 mg, 0.578 mmol) in THF (4 mL) and water (2.0 mL) was added LiOH (69.3 mg, 2.89 mmol) and the reaction mixture was stirred at RT for 40 h. Another aliquot of LiOH was added (69.3 mg, 2.89 mmol). Stirring was continued at RT for 60 h and subsequently at 50° C. for 16 h to complete the reaction. Water was added and volatiles were removed under reduced pressure. The aqueous phase was adjusted to pH 2 to 3 by addition of 1N aqueous HCl, followed by extraction with EtOAC (3×). The combined organics were dried (Phase separator) and concentrated in vacuo to give the title compound as a white solid. MS (LC/MS): 262 [M+Na]+, 190 [MH−tBu]+, 146 [MH−Boc]+, tR (HPLC conditions b): 3.51 min.

後処理

  1. stirringStirring
  2. waitwas continued at RT for 60 h and subsequently at 50° C. for 16 h
  3. customthe reaction
  4. customvolatiles were removed under reduced pressure
  5. additionThe aqueous phase was adjusted to pH 2 to 3 by addition of 1N aqueous HCl
  6. extractionfollowed by extraction with EtOAC (3×)
  7. customThe combined organics were dried (Phase separator)
  8. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-84255e7b4aa44ffaa136cd4b2c2e9db0
出典データセット
uspto-grants-2015_07
特許番号
US09085555B2

反応ノート

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