Sodium borohydride → rac-tert-butyl (3aR,5R,6aS)-5-hydroxy-octahydrocyclopenta(c)pyrrole-2-carboxylate

HRID 1752350ノート

反応式

HRID 1752350 の反応式
[BH4-].[Na+].[O:3]=[C:4]1[CH2:18][C@@H:7]2[CH2:8][N:9]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:10][C@@H:6]2[CH2:5]1>CO>[OH:3][CH:4]1[CH2:18][C@@H:7]2[CH2:8][N:9]([C:11]([O:13][C:14]([CH3:16])([CH3:15])[CH3:17])=[O:12])[CH2:10][C@@H:6]2[CH2:5]1

参加物

4

反応物 2

HCID 4311764Sodium borohydrideHCID 10998692cis-5-Oxohexahydrocyclopenta[c]pyrrole-2(1H)-carboxylic acid tert-butyl ester

生成物 1

HCID 20753133rac-tert-butyl (3aR,5R,6aS)-5-hydroxy-octahydrocyclopenta(c)pyrrole-2-carboxylate収率 98%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

Sodium borohydride (0.15 g, 4.00 mmol), was added to a solution of 1,1-dimethylethyl(3aR,6aS)-5-oxo-hexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate (0.45 g, 2.00 mmol) in 10 mL methanol at 0° C. and the reaction mixture was stirred for 1 h at this temperature. The solvent was evaporated, the crude mixture was diluted with 100 mL ethyl acetate and washed with water (30 mL), 1M aqueous hydrochloric acid and brine. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated to give 1,1-dimethylethyl(3aR,6aS)-5-(hydroxy)-hexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate (0.44 g, 98%). 1H NMR (400 MHz, d6-DMSO): 4.08 (m, 1H), 3.40 (m, 2H), 3.30 (m, 2H), 2.50 (m, 2H), 1.98 (m, 2H), 1.40 (s, 9H), 1.30 (m, 2H). MS (EI) for C12H21NO3: 228 (MH+).

後処理

  1. customThe solvent was evaporated
  2. additionthe crude mixture was diluted with 100 mL ethyl acetate
  3. washwashed with water (30 mL), 1M aqueous hydrochloric acid and brine
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-d9962ed25ad644c1a884d07657b6aced
出典データセット
uspto-grants-2015_10
特許番号
US09163006B2

反応ノート

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