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HRID69986

反应详情

EQUATION

反应方程式

HRID 69986 的结构方程式

REACTANTS

反应物

4
结构：O=C(O)CC(O)(CC(=O)O)C(=O)O
HCID311

Citric Acid

C6H8O7

结构：[Cl-].[Li+]
HCID433294

Lithium Chloride

ClLi

结构：[BH4-].[Na+]
HCID4311764

Sodium borohydride (Na(BH4))

H4BNa

结构：COC(=O)[C@H]1C[C@@H](NC(=O)OC(C)(C)C)CN(C(=O)OCc2ccccc2)C1
HCID95731685

未命名化合物

PRODUCTS

生成物

1
结构：CC(C)(C)OC(=O)N[C@H]1C[C@@H](CO)CN(C(=O)OCc2ccccc2)C1
HCID131729683

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

1
结构：C1CCOC1
溶剂HCID8028

Tetrahydrofuran

C4H8O

PROCEDURE

实验过程

A solution of cis (+/−)-1-benzyl 3-methyl 5-(tert-butoxycarbonylamino)piperidine-1,3-dicarboxylate (1.0 eq.) in THF at a concentration of 0.08 M was cooled at 0*C and then LiCl (2.3 eq.) and sodium borohydride (2.3 eq.) were added. After stirring for 20 hours as the reaction warmed to rt, the pH was adjusted with 1M citric acid to pH 4-5. After removal of the volatiles in vacuo, the product was extracted in dichloromethane, washed with H2O and brine, dried over MgSO4. Upon filtering and removal of the volatiles in vacuo, cis (+/−)-benzyl 3-(tert-butoxycarbonylamino)-5-(hydroxymethyl)piperidine-1-carboxylate was obtained as a white foamy solid. LCMS (m/z): 265.0 (MH-Boc+); LC Rt=3.37 min.

WORKUP

后处理

  1. customAfter removal of the volatiles in vacuo
  2. extractionthe product was extracted in dichloromethane
  3. washwashed with H2O and brine
  4. dry with materialdried over MgSO4
  5. filtrationUpon filtering
  6. customremoval of the volatiles in vacuo