Sodium borohydride → HCID 54087274, compound

HRID 981040Notes

Reaction equation

HRID 981040 reaction equation
[CH2:1]([O:8][C:9]([C@H:11]1[CH2:14][C@@H:13]([C:15](OCC2C=CC=CC=2)=[O:16])[N:12]1[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:10])[C:2]1C=CC=CC=1.[BH4-].[Na+]>C(O)C>[CH2:1]([O:8][C:9]([CH:11]1[CH2:14][CH:13]([CH2:15][OH:16])[N:12]1[CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)=[O:10])[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 14654393HCID 14654393, compound2×

Product 1

HCID 54087274HCID 54087274, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

This compound is obtained, as the result of a concomitant transesterification, when NaBH4 reduction is applied directly to cis-N-benzylazetidine-2,4-dicarboxylic acid dibenzyl ester. To 104 mg (0.25 mmol) of cis-N-benzylazetidine-2,4-dicarboxylic acid dibenzyl ester in 2.5 ml of absolute ethanol is added, at r.t. in small portions over a period of 1 h, 45 mg (1.25 mmol) of NaBH4. Quenching with 50 μl of acetic acid is followed by filtration through a medium porosity sintered glass funnel, repeated washing of the solids with methylene chloride, and evaporation. The residue is chromatographed on SiO2 ; EtOAc/hexanes (1:3) elutes benzyl alcohol, EtOAc/hexanes (1:1) the product. The product is a colorless oil obtained in 39.8 mg (64%) yield. 1H NMR (CDCl3): δ7.35-7.25 (m, 5H), 4.09 (q, 2H, J=7), 3.84, 3.67 (AB system, 2H, J=12.5), 3.66 (t, 1H, J=8.5), 3.38 (tt, 1H, J=8, 2.5), 3.25-3.15 (m, 2H), 2.81 (br., 1H), 2.37-2.21 (m, 2H), 1.20 (t, 3H, J=7). IR (neat): 3432, 3063, 2928, 2870, 1736, 1495, 1455, 1194, 1096, 1034, 961, 739, 704 cm-1.

Workup

  1. customQuenching with 50 μl of acetic acid
  2. filtrationis followed by filtration through a medium porosity sintered glass funnel
  3. washrepeated washing of the solids with methylene chloride, and evaporation
  4. customThe residue is chromatographed on SiO2
  5. customobtained in 39.8 mg (64%)
  6. customyield

Sources & evidence

ORD record
ord-c2187d5dd9274895860ec4fd4ddd75fe
Source dataset
uspto-grants-1991_02
Patent number
US04990504

Reaction notes

Loading…