Hydrochloric Acid → (2S,4S)-1-[(benzyloxy)carbonyl]-4-cyclohexylpyrrolidine-2-carboxylic acid

HRID 280380ノート

反応式

HRID 280380 の反応式
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@H:14]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[CH2:13][C@H:12]1[CH2:22][OH:23])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=[O:25].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.Cl>CN(C)C=O>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@H:14]([CH:16]2[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]2)[CH2:13][C@H:12]1[C:22]([OH:25])=[O:23])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 2724130Cornforth reagentHCID 13648262(2S-trans)-1-[(Benzyloxy)carbonyl]-4-cyclohexyl-2-pyrrolidinemethanol

生成物 1

HCID 54164240(2S,4S)-1-[(benzyloxy)carbonyl]-4-cyclohexylpyrrolidine-2-carboxylic acid収率 58.9%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of (2S-trans)-1-[(benzyloxy)carbonyl]-4-cyclohexyl-2-pyrrolidinemethanol (0.65 g) in dimethylformamide (10 ml) was added pyridinium dichromate (2.1 g). The mixture was stirred at room temperature for 16 hours and poured into crushed ice and hydrochloric acid (25 ml). Extraction with ethyl acetate followed by solvent evaporation yielded 0.4 g of (trans)-1-[(benzyloxy)carbonyl]-4-cyclohexyl-L-proline as a thick oil. The compound can be deprotected using catalytic hydrogenation as described in Method V.

後処理

  1. additionpoured
  2. extractionExtraction with ethyl acetate
  3. customfollowed by solvent evaporation

出典と根拠

ORDレコード
ord-87bf334af2304eeab2960cb2be1865ee
出典データセット
uspto-grants-1986_05
特許番号
US04588819

反応ノート

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