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HRID1455404

反应详情

EQUATION

反应方程式

HRID 1455404 的结构方程式

REACTANTS

反应物

3
结构：O
HCID962

Water

H2O

结构：[BH4-].[Na+]
HCID4311764

Sodium borohydride (Na(BH4))

H4BNa

结构：CC(C)(C)OC(=O)N1C(=O)[C@@H]2C[C@H]1CC[C@@H]2N1CC[C@H](NC(=O)OCc2ccccc2)C1=O
HCID67182479

未命名化合物

PRODUCTS

生成物

1
结构：CC(C)(C)OC(=O)N[C@@H]1CC[C@H](N2CC[C@H](NC(=O)OCc3ccccc3)C2=O)[C@H](CO)C1
HCID68767819

未命名化合物

收率 104.1%

AUXILIARIES

试剂、催化剂与溶剂

1
结构：C1CCOC1
溶剂HCID8028

Tetrahydrofuran

C4H8O

PROCEDURE

实验过程

(1R,2S,5R)-Tert-butyl 2-((S)-3-(benzyloxycarbonylamino)-2-oxopyrrolidin-1-yl)-7-oxo-6-aza-bicyclo[3.2.1]octane-6-carboxylate (2.0 g) was dissolved in THF (50 mL) and water (15 mL) prior to the addition of NaBH4 (827 mg). After 5 h, the reaction was quenched with saturated NaHCO3 solution and extracted with EtOAc (2×). The organic extracts were combined, dried (MgSO4), filtered, and concentrated in vacuo to afford tert-butyl (1R,3R,4S)-4-((S)-3-benzyloxycarbonylamino-2-oxopyrrolidin-1-yl)-3-(hydroxymethyl)cyclohexylcarbamate (2.1 g). MS (ES+)=462.5 (M+H)+.

WORKUP

后处理

  1. customthe reaction was quenched with saturated NaHCO3 solution
  2. extractionextracted with EtOAc (2×)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo