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Sodium borohydride → tert-butyl[(2S)-1-{[tert-butyl(diphenyl)silyl]oxy}-6-hydroxyhexan-2-yl]carbamate

HRID 1524345
ノート
印刷プレビュー

反応式

HRID 1524345 の反応式
C(OC(=O)N[C:8](=[O:40])[CH2:9][CH2:10][CH2:11][C@H:12]([NH:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:13][O:14][Si:15]([C:28]([CH3:31])([CH3:30])[CH3:29])([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(C)(C)C.[BH4-].[Na+]>CC(O)C.O>[C:36]([O:35][C:33](=[O:34])[NH:32][C@@H:12]([CH2:11][CH2:10][CH2:9][CH2:8][OH:40])[CH2:13][O:14][Si:15]([C:28]([CH3:29])([CH3:30])[CH3:31])([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)([CH3:39])([CH3:37])[CH3:38]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 4311764Sodium borohydride2 回HCID 89938443tert-butyl[(5S)-5-[(tert-butoxycarbonyl)amino]-6-{[tert-butyl(diphenyl)silyl]oxy}hexanoyl]carbamate

生成物 1

HCID 89938349tert-butyl[(2S)-1-{[tert-butyl(diphenyl)silyl]oxy}-6-hydroxyhexan-2-yl]carbamate収率 62.9%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 3776
Isopropanol
溶媒

実験手順

To a stirred solution of the material from Step 3 (128 g, 219 mmol) in 2-propanol (1800 mL) and water (180 mL) at room temperature was added sodium borohydride (8.28 g, 219 mmol). The reaction mixture was stirred at room temperature overnight. Additional 2 g of sodium borohydride was added and stirred at room temperature for an additional 4 hours. The reaction mixture was concentrated to ⅓ volume and diluted with EtOAc and 1 N NaOH (100 mL). The reaction mixture was partitioned, and extracted with EtOAc. The combined organics were washed with brine, dried over MgSO4, filtered and concentrated. The residue was purified by flash chromatography on silica gel using EtOAc-hexanes (0 to 50%) to afford 65 g of the title compound. 1H NMR (CHCl3-d): δ 7.67-7.62 (m, 4H), 7.45-7.35 (m, 6H), 4.72-4.65 (b, 1H), 3.72-3.62 (m, 2H), 3.60-3.52 (m, 3H), 1.62-1.42 (m, 4H), 1.42 (s, 9H), 1.42-1.23 (m, 2H), 1.05 (s, 9H).

後処理

  1. stirringstirred at room temperature for an additional 4 hours
  2. concentrationThe reaction mixture was concentrated
  3. additiondiluted with EtOAc and 1 N NaOH (100 mL)
  4. customThe reaction mixture was partitioned
  5. extractionextracted with EtOAc
  6. washThe combined organics were washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was purified by flash chromatography on silica gel

出典と根拠

ORDレコード
ord-1fc34a7d23f0442fbb866fd0d1bc94d9
出典データセット
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09079834B2

反応ノート

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