Sodium borohydride → (Meso-3aR,5r,6aS)-tert-butyl 5-hydroxyhexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate

HRID 446714ノート

反応式

HRID 446714 の反応式
[O:1]=[C:2]1[CH2:16][C@@H:5]2[CH2:6][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:8][C@@H:4]2[CH2:3]1.[BH4-].[Na+]>C(O)C>[OH:1][CH:2]1[CH2:16][C@@H:5]2[CH2:6][N:7]([C:9]([O:11][C:12]([CH3:14])([CH3:13])[CH3:15])=[O:10])[CH2:8][C@@H:4]2[CH2:3]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 20753133(Meso-3aR,5r,6aS)-tert-butyl 5-hydroxyhexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate収率 93%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

Compound 1019 (4 g; 0.018 mole) was dissolved in 50 mL of ethanol. Sodium borohydride was added at RT portionwise. After stirring for 3 hours, the reaction was concentrated in vacuo. The resulting oil was dissolved in DCM (200 mL), washed with water, brine, (Na2SO4), and concentrated in vacuo to yield (3aR,6aS)-tert-butyl 5-hydroxyhexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate as a yellow oil (Compound 1020, 3.79 g; 93% yield); 1H NMR (CDCl3): δ 4.2 (m, 1H), 3.55 (dd, 2H), 3.4 (dd, 2H), 2.7 (m, 2H), 2.2 (m, 2H), 1.6 (m, 2H), 1.5 (s, 9H).

後処理

  1. concentrationthe reaction was concentrated in vacuo
  2. dissolutionThe resulting oil was dissolved in DCM (200 mL)
  3. washwashed with water, brine, (Na2SO4),
  4. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-cdf34d82b69745e7bb8e7b385814cb35
出典データセット
uspto-grants-2013_07
特許番号
US08481524B2

反応ノート

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