Hydrochloric Acid → HCID 178499257, compound

HRID 1694435Notes

Reaction equation

HRID 1694435 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([Br:27])=[CH:8][C:9]=1[N:10]([C:18]([C@H:20]1[CH2:25][CH2:24][C@H:23]([CH3:26])[CH2:22][CH2:21]1)=[O:19])[CH:11]1[CH2:16][CH2:15][C:14](=[O:17])[CH2:13][CH2:12]1)=[O:4].[BH4-].[Na+].CCCCCC.CCOC(C)=O.Cl>CO>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([Br:27])=[CH:8][C:9]=1[N:10]([C@H:11]1[CH2:12][CH2:13][C@H:14]([OH:17])[CH2:15][CH2:16]1)[C:18]([C@H:20]1[CH2:21][CH2:22][C@H:23]([CH3:26])[CH2:24][CH2:25]1)=[O:19])=[O:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 21226206Ethyl acetate hexaneHCID 178499251HCID 178499251, compound

Product 1

HCID 178499257HCID 178499257, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a cold (0° C.) solution of 5-Bromo-3-[(trans-4-methyl-cyclohexanecarbonyl)-(4-oxo-cyclohexyl)-amino]-thiophene-2-carboxylic acid methyl ester (5.9 g, 12.9 mmol) in 50 ml of MeOH under a positive N2 add NaBH4 (250 mg, 6.4 mmol, 0.5 eq.) portion wise (approx. 30 minutes). After the addition is completed, check for reaction completion by TLC Hexane:EtOAc 1:1). Add 10 ml of HCl 2% and stirred for 15 min. The reaction mixture was concentrated under vacuum to dryness. The reaction mixture was recuperated with water (25 ml) and extracted with EtOAC. The organic phases were combined and dried over MgSO4 and concentrated to dryness. The residue was purified by silica gel column chromatography using EtOAc:hexanes as eluent to obtain 5-Bromo-3-[(trans-4-hydroxy-cyclohexyl)-(trans-4-methyl-cyclohexane-carbonyl)-amino]-thiophene-2-carboxylic acid methyl ester (4.5 g, 77% yield) as a solid.

Workup

  1. additionAfter the addition
  2. concentrationThe reaction mixture was concentrated under vacuum to dryness
  3. extractionextracted with EtOAC
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated to dryness
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f6c4a6b479e9495092991cdb67cab5f5
Source dataset
uspto-grants-2012_04
Patent number
US08158675B2

Reaction notes

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