Sodium borohydride → (3R,4R)-benzyl 3-amino-4-(tosyloxy)piperidine-1-carboxylate

HRID 1254409ノート

反応式

HRID 1254409 の反応式
[BH4-].[Na+].[N:3]([C@H:6]1[C@H:11]([O:12][S:13]([C:16]2[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=2)(=[O:15])=[O:14])[CH2:10][CH2:9][N:8]([C:23]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:24])[CH2:7]1)=[N+]=[N-]>CO>[NH2:3][C@H:6]1[C@H:11]([O:12][S:13]([C:16]2[CH:17]=[CH:18][C:19]([CH3:20])=[CH:21][CH:22]=2)(=[O:14])=[O:15])[CH2:10][CH2:9][N:8]([C:23]([O:25][CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)=[O:24])[CH2:7]1

参加物

4

反応物 2

HCID 4311764Sodium borohydride2 回HCID 59201561HCID 59201561、化合物

生成物 1

HCID 59201320(3R,4R)-benzyl 3-amino-4-(tosyloxy)piperidine-1-carboxylate収率 64.5%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

To a cooled (0° C., ice/water bath) solution of CuSO4.5H2O (642 mg, 0.5 equiv) in methanol (30 mL) was added slowly NaBH4 (200 mg, 1.05 equiv). To the stirred black suspension was added a solution of (3R,4R)-benzyl 3-azido-4-(tosyloxy)piperidine-1-carboxylate (2.21 g, 5.14 mmol) in methanol (20 mL). Additional NaBH4 (578 mg, 3 equiv) was introduced into the reaction in four portions over the course of 1 h. LC-MS showed the reaction was complete. The reaction mixture was filtered through a pad of Celite, and concentrated. The residue was diluted with CH2Cl2 (70 mL), washed with water (15 mL), satd aq NH4Cl solution (2×10 mL) and brine (15 mL), and dried over Na2SO4. Concentration afforded (3R,4R)-benzyl 3-amino-4-(tosyloxy)piperidine-1-carboxylate (1.34 g, 64%). LC-MS (3 min) tR=1.26 min., m/z 405 (M+1). The product was used for the next step without further purification.

後処理

  1. filtrationThe reaction mixture was filtered through a pad of Celite
  2. concentrationconcentrated
  3. additionThe residue was diluted with CH2Cl2 (70 mL)
  4. washwashed with water (15 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationConcentration

出典と根拠

ORDレコード
ord-c6b6921da89043ee8178665c387f45f6
出典データセット
uspto-grants-2013_06
特許番号
US08455521B2

反応ノート

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