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Sodium triacetoxyborohydride → tert-butyl (2S,3R)-4-((5-(2-fluoropropan-2-yl)pyridin-3-yl)methylamino)-3-hydroxy-1-phenylbutan-2-ylcarbamate

HRID 2071181
ノート
印刷プレビュー

反応式

HRID 2071181 の反応式
[NH2:1][CH2:2][C@@H:3]([OH:20])[C@@H:4]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[F:21][C:22]([C:25]1[CH:26]=[N:27][CH:28]=[C:29]([CH:32]=1)[CH:30]=O)([CH3:24])[CH3:23].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C1COCC1.C(O)(=O)C.CCOC(C)=O>[F:21][C:22]([C:25]1[CH:32]=[C:29]([CH2:30][NH:1][CH2:2][C@@H:3]([OH:20])[C@@H:4]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:17])([CH3:16])[CH3:18])[CH2:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:28]=[N:27][CH:26]=1)([CH3:24])[CH3:23]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 5049666Sodium triacetoxyborohydrideHCID 10333883tert-butyl (2S,3R)-4-amino-3-hydroxy-1-phenylbutan-2-ylcarbamateHCID 595701465-(2-Fluoropropan-2-yl)nicotinaldehyde

生成物 1

HCID 59569922tert-butyl (2S,3R)-4-((5-(2-fluoropropan-2-yl)pyridin-3-yl)methylamino)-3-hydroxy-1-phenylbutan-2-ylcarbamate収率 70%

試薬・触媒・溶媒 3

HCID 176
Acetic Acid
触媒
HCID 8028Tetrahydrofuran溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

A solution of tert-butyl (2S,3R)-4-amino-3-hydroxy-1-phenylbutan-2-ylcarbamate (297 mg, 1.06 mmol) in THF was added 5-(2-fluoropropan-2-yl)nicotinaldehyde (180 mg, 1.06 mmol) and stirred for 30 min at room temperature, NaB(OAc)3H (460 mg, 2.12 mmol) was then added portionwise in 30 min., finally 5 drops of acetic acid was added and the resulting mixture was stirred at the same temperature overnight. The reaction mixture was diluted with EtOAc, and washed with saturated aqueous NaHCO3. The organic layer was separated and dried (MgSO4). Concentration in vacuo, followed purification with flash chromatography to give tert-butyl (2S,3R)-4-((5-(2-fluoropropan-2-yl)pyridin-3-yl)methylamino)-3-hydroxy-1-phenylbutan-2-ylcarbamate as a white solid (230 mg, 70% yield). 1H NMR (CDCl3): d: 8.776 (d, J=11.5 Hz, 2H), 7.952 (s, 1H), 7.330-7.205 (m, 5H), 4.823 (d, J=7.7 Hz, 1H), 3.900 (s, 2H), 3.842 (m, 1H), 3.586 (m, 1H), 2.995 (m, 1H), 2.856 (m, 1H), 2.762 (m, 2H), 1.363 (s, 9H).

後処理

  1. stirringthe resulting mixture was stirred at the same temperature overnight
  2. washwashed with saturated aqueous NaHCO3
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. concentrationConcentration in vacuo
  6. custompurification with flash chromatography

出典と根拠

ORDレコード
ord-99e4c6f481a047d7bf3c6463b45fafd2
出典データセット
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08299267B2

反応ノート

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