Acetic Acid → (+-)(2R*,3R*)-2-amino-2-methyl-1,3-butanediol acetate

HRID 1165655노트

반응식

HRID 1165655 반응식
[CH3:1][C@:2]([N+:8]([O-])=O)([C@H:5]([OH:7])[CH3:6])[CH2:3][OH:4].[C:11]([OH:14])(=[O:13])[CH3:12]>CCO.[Pd]>[C:11]([OH:14])(=[O:13])[CH3:12].[NH2:8][C@@:2]([CH3:1])([C@H:5]([OH:7])[CH3:6])[CH2:3][OH:4]

참가 물질

5

반응물 2

HCID 176Acetic AcidHCID 13375425(+-)(2R*,3R*)-2-Methyl-2-nitro-1,3-butanediol

생성물 1

HCID 86741969(+-)(2R*,3R*)-2-amino-2-methyl-1,3-butanediol acetate

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

To a solution of (±)-(2R*,3R*)-2-methyl-2-nitro-1,3-butanediol (32B, 13.93 g, 0.093 mol) in 95% EtOH (120 mL) was added glacial acetic acid (17 mL) and 10% Pd/C (MCB, 1.0 g). The mixture was reduced in a Parr apparatus at 50 psi of H2 for 48 h. The catalyst was then removed by filtration on a Celite® pad and the solvent removed to give the crude amine salt. Three portions of PhCH3 (50 mL) were added to the flask and removed by rotary evaporation to remove final traces of H2O and acetic acid. The residue, a viscous oil gradually solidified under high vacuum. The solie was triturated with Et2O, filtered and the resulting solid further washed with Et2O to give after drying, 16.23 g (97%) of (±)-(2R*,3R*)-2-amino-2-methyl-1,3-butanediol acetate, mp 117°-121°, (C,H,N).

후처리

  1. customThe catalyst was then removed by filtration on a Celite® pad
  2. customthe solvent removed

출처 및 근거

ORD 기록
ord-4295bad2369d4da2a1ecf2e24495406a
출처 데이터셋
uspto-grants-1990_03
특허 번호
US04910218

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