Potassium bisulfate → 3-[(3,4-Dichloro-phenyl)-(2-hydroxy-ethyl)-amino]-propionic Acid tert-butyl ester

HRID 1096196Notes

Reaction equation

HRID 1096196 reaction equation
[C:1]([O:5][C:6](=[O:23])[CH2:7][CH2:8][N:9]([C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Cl:22])[CH:16]=1)[CH2:10][C:11](OC)=[O:12])([CH3:4])([CH3:3])[CH3:2].[Li+].[BH4-].OS([O-])(=O)=O.[K+]>>[C:1]([O:5][C:6](=[O:23])[CH2:7][CH2:8][N:9]([C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Cl:22])[CH:16]=1)[CH2:10][CH2:11][OH:12])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 3

HCID 516920Potassium bisulfateHCID 4148881Lithium borohydride2×HCID 667831343-[(3,4-Dichloro-phenyl)-methoxycarbonylmethyl-amino]-propionic Acid tert-butyl ester

Product 1

HCID 667832343-[(3,4-Dichloro-phenyl)-(2-hydroxy-ethyl)-amino]-propionic Acid tert-butyl esterYield 85.4%

Conditions

Temperature
0 °C

Procedure

A solution of 7.76 g (21.43 mmol) of 3-[(3,4-dichloro-phenyl)-methoxycarbonylmethyl-amino]-propionic acid tert-butyl ester in 250 ml of ETOH was treated at 0° C. with 0.98 g (42.86 mmol) of LiBH4. The reaction was stirred 10 min at 0° C. and 15 h at RT. After cooling (0° C.) a second batch of 0.49 g (21.43 mmol) of LiBH4 was added and stirred 6 h at RT. The reaction was cooled (0° C.), neutralized with aq. 10% KHSO4 solution and extracted with EtOAc (3×). The organic phase was dried over Na2SO4 evaporated and purified by flash silica gel column (n-heptane:EtOAc 9:1 to 1:1) to yield 6.12 g (85%) of the title compound as light yellow oil. MS: 334.2 (MH+, 2Cl).

Workup

  1. additionwas added
  2. stirringstirred 6 h at RT
  3. temperatureThe reaction was cooled (0° C.)
  4. extractionextracted with EtOAc (3×)
  5. dry with materialThe organic phase was dried over Na2SO4
  6. customevaporated
  7. custompurified by flash silica gel column (n-heptane:EtOAc 9:1 to 1:1)

Sources & evidence

ORD record
ord-414e282f6c1942adb86db72b3c2f2a9a
Source dataset
uspto-grants-2012_03
Patent number
US08138175B2

Reaction notes

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