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Dichloromethane → (2S,4S)-2-(3-Chloro-2-fluoro-benzylcarbamoyl)-4-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 1527321
ノート
印刷プレビュー

反応式

HRID 1527321 の反応式
C[O:2][C:3]([C@H:5]1[CH2:9][C@@H:8]([C:10](=[O:21])[NH:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[C:14]=2[F:20])[N:7]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:6]1)=O.[BH4-].[Li+].C(Cl)Cl>C1COCC1.[Cl-].[Na+].O>[C:25]([O:24][C:22]([N:7]1[CH2:6][C@@H:5]([CH2:3][OH:2])[CH2:9][C@H:8]1[C:10](=[O:21])[NH:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[C:14]=1[F:20])=[O:23])([CH3:28])([CH3:26])[CH3:27]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 6344DichloromethaneHCID 4148881Lithium borohydrideHCID 68284043(3S,5S)-5-(3-Chloro-2-fluoro-benzylcarbamoyl)-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester

生成物 1

HCID 68283501(2S,4S)-2-(3-Chloro-2-fluoro-benzylcarbamoyl)-4-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

試薬・触媒・溶媒 2

HCID 8028
Tetrahydrofuran
溶媒
HCID 57417360Sodium chloride; water溶媒

実験手順

To a solution (3S,5S)-5-(3-chloro-2-fluoro-benzylcarbamoyl)-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester (550 mg, 1.33 mmol) in THF (6 mL) was added lithium borohydride (2 M in THF, 1.46 mL, 2.92 mmol) at RT and the mixture was further stirred for 2 h under N2 atmosphere. After completion brine and CH2Cl2 were added, the layers were separated and the aqueous one re-extracted with CH2Cl2. The combined organic layers were dried (MgSO4), filtered and concentrated. The crude was purified by flash column chromatography on silica gel (eluent: EtOAc) to give the desired material. MS (LC/MS): 409.1 [M+Na]+, 287.0 [MH−Boc]+, 385.1 [M−H]−; tR (HPLC conditions f): 1.82 min.

後処理

  1. customthe layers were separated
  2. extractionthe aqueous one re-extracted with CH2Cl2
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude was purified by flash column chromatography on silica gel (eluent: EtOAc)

出典と根拠

ORDレコード
ord-afd96f09b8a74490ac36b0e70e6431d4
出典データセット
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09085555B2

反応ノート

読み込み中…

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