Water → (R)-tert-butyl 1-bromopropan-2-ylcarbamate

HRID 1053676ノート

反応式

HRID 1053676 の反応式
O[CH2:2][C@H:3]([NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])[CH3:4].C(Br)(Br)(Br)[Br:14].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>C(Cl)Cl>[Br:14][CH2:2][C@H:3]([NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])[CH3:4]

参加物

6

反応物 4

HCID 962WaterHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 13200309tert-butyl N-((2R)-1-hydroxypropan-2-yl)carbamate

生成物 1

HCID 57081792(R)-tert-butyl 1-bromopropan-2-ylcarbamate収率 50.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

(R)-tert-Butyl 1-hydroxypropan-2-ylcarbamate (1.00 g, 5.71 mmol) and carbon tetrabromide (2.84 g, 8.56 mmol) were stirred in CH2Cl2 (20 mL) at −20° C. under argon. A solution of triphenylphosphine (2.40 g, 9.13 mmol) in CH2Cl2 (5 mL) was added dropwise. The reaction was allowed to reach rt and stirred for 14 h. H2O (50 mL) was added to the reaction mixture and then the aqueous layer was removed and the CH2Cl2 layer was dried over Na2SO4, filtered, and evaporated. The residue was applied to a silica gel column and eluted with 5:1 hexanes/EtOAc. Intermediate 7A (0.68 g, 2.86 mmol, 50% yield) was isolated as a white solid. LC-MS (ESI) 183.9 (M-tBu+H), RT=1.76 min (Method B).

後処理

  1. customto reach rt
  2. customthe aqueous layer was removed
  3. dry with materialthe CH2Cl2 layer was dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. washeluted with 5:1 hexanes/EtOAc

出典と根拠

ORDレコード
ord-93b651d77eee4ecf84a1621f8fe62993
出典データセット
uspto-grants-2016_07
特許番号
US09394260B2

反応ノート

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