Carbon tetrabromide → 3-Bromo-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 42135노트

반응식

HRID 42135 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10](O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:34]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([Br:34])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

5

반응물 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 44169391-Boc-3-pyrrolidinol

생성물 1

HCID 426142173-Bromo-pyrrolidine-1-carboxylic acid tert-butyl ester수율 80%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of (RS) 1-tert-butoxycarbonyl-3-pyrrolidinol (Prepn. 3) (3.00 g) in THF (90 mL), triphenylphosphine (12.4 g) was added, then a solution of CBr4 (15.7 g) in THF (90 mL) was dropped and the mixture stirred overnight at room temperature. The organic solvent was evaporated and the residue was extracted with EtOAc (4×50 mL). The combined organic extracts were washed with H2O, dried over Na2SO4 and evaporated to dryness. The residue was purified by flash chromatography (SiO2, cyclohexane/EtOAc 80/20) to give (RS) 1-tert-butoxycarbonyl-3-bromopyrrolidine in 80% yield as yellow oil. 1H-NMR (300 MHz, DMSO-d6, ppm from TMS): δ 4.85 (1H, m), 3.70-3.59 (1H, m), 3.55-2.10 (5H, m), 1.35 (9H, s).

후처리

  1. customThe organic solvent was evaporated
  2. extractionthe residue was extracted with EtOAc (4×50 mL)
  3. washThe combined organic extracts were washed with H2O
  4. dry with materialdried over Na2SO4
  5. customevaporated to dryness
  6. customThe residue was purified by flash chromatography (SiO2, cyclohexane/EtOAc 80/20)

출처 및 근거

ORD 기록
ord-35f8915470a1418a81cdc37cf87deb5f
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536160B2

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