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

HRID 42135ノート

反応式

HRID 42135 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-35f8915470a1418a81cdc37cf87deb5f
出典データセット
uspto-grants-2013_09
特許番号
US08536160B2

反応ノート

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