Carbon tetrabromide → methyl (1R,3S)-3-(bromomethyl)cyclopentane-1-carboxylate

HRID 537364ノート

反応式

HRID 537364 の反応式
O[CH2:2][C@H:3]1[CH2:7][CH2:6][C@@H:5]([C:8]([O:10][CH3:11])=[O:9])[CH2:4]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:32]>C(Cl)Cl>[Br:32][CH2:2][C@H:3]1[CH2:7][CH2:6][C@@H:5]([C:8]([O:10][CH3:11])=[O:9])[CH2:4]1

参加物

5

反応物 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 13425819rac-methyl (1R,3S)-3-(hydroxymethyl)cyclopentane-1-carboxylate

生成物 1

HCID 67111244methyl (1R,3S)-3-(bromomethyl)cyclopentane-1-carboxylate収率 31.7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a 0° C. solution of 99 (6.6 gm, 50 mmol, 1 equi.) in 60 mL of DCM was added triphenyl phosphine (60 mmol, 1.2 equi, 15.72 gm) followed by carbon tetrabromide (60 mmol, 1.2 equi. 19.86 gm). The reaction mixture was stirred overnight allowing the temperature to rise to room temperature. Reaction was concentrated to dryness and the residue was diluted with ether/DCM (1:1, 20 ml) and filtered through a pad of celite. The filtrate was concentrated to dryness and the residue was purified by silica gel chromatography with (5% to 20% EtOAc in hexanes) to provide 3.5 g of (1R,3S)-methyl 3-(bromomethyl)cyclopentanecarboxylate 100.

後処理

  1. customto rise to room temperature
  2. customReaction
  3. concentrationwas concentrated to dryness
  4. additionthe residue was diluted with ether/DCM (1:1, 20 ml)
  5. filtrationfiltered through a pad of celite
  6. concentrationThe filtrate was concentrated to dryness
  7. customthe residue was purified by silica gel chromatography with (5% to 20% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-0647b60b1b9a49d6853e74140732664d
出典データセット
uspto-grants-2014_10
特許番号
US08859776B2

反応ノート

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