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

HRID 1425532노트

반응식

HRID 1425532 반응식
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.C1C=C2C(C(O)(O)C(=O)C2=CC=1)=O>>[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]

참가 물질

5

반응물 4

HCID 10236NinhydrinHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 13200309tert-butyl N-((2R)-1-hydroxypropan-2-yl)carbamate

생성물 1

HCID 57081792(R)-tert-butyl 1-bromopropan-2-ylcarbamate수율 49.3%

실험 절차

A solution of (R)-tert-butyl 1-hydroxypropan-2-ylcarbamate (100 mg, 571 μmol) and carbon tetrabromide (303 mg, 913 μmol) was cooled on an ice bath. Triphenylphosphine (299 mg, 1141 μmol) was added and the reaction was stirred for 10 min. The reaction was then allowed to warm to r.t. and stirred for 18 hours. After this time, a TLC suggested that the reaction was complete (silica, 50% EtOAc/Hexanes, Ninhydrin stain). The solvent was removed and the product purified by column chromatography (0,5,10,15,20% EtOAc/Hexanes) to yield (R)-tert-butyl 1-bromopropan-2-ylcarbamate (67.1 mg, 0.28 mmol, 49.3%) as a colorless oil that turned solid upon standing. LCMS 238.1 (M+H); 1H NMR (400 MHz, MeOH-d4) δ ppm 1.23 (d, J=6.57 Hz, 3 H), 1.46 (s, 9 H), 3.44 (dd, J=5.56, 1.77 Hz, 2 H), 3.71-3.92 (m, 1 H).

후처리

  1. stirringstirred for 18 hours
  2. customThe solvent was removed
  3. customthe product purified by column chromatography (0,5,10,15,20% EtOAc/Hexanes)

출처 및 근거

ORD 기록
ord-667fbf4778c949cfad356013c335ebb3
출처 데이터셋
uspto-grants-2015_01
특허 번호
USRE045336E1

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