Hydrochloric Acid → (1R,2R,4R)-2-(tert-butoxycarbonyl)-4-(tert-butyldiphenylsilyloxy)cyclohexanecarboxylic acid

HRID 530707Notes

Reaction equation

HRID 530707 reaction equation
C[O:2][C:3]([C@@H:5]1[CH2:10][CH2:9][C@@H:8]([O:11][Si:12]([C:25]([CH3:28])([CH3:27])[CH3:26])([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:7][C@H:6]1[C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[O:4].[Li+].[OH-].Cl>C1COCC1.O>[C:32]([O:31][C:29]([C@@H:6]1[CH2:7][C@H:8]([O:11][Si:12]([C:25]([CH3:28])([CH3:27])[CH3:26])([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:9][CH2:10][C@H:5]1[C:3]([OH:4])=[O:2])=[O:30])([CH3:35])([CH3:33])[CH3:34]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58282737(1R,2R,4R)-2-tert-butyl 1-methyl 4-(tert-butyldiphenylsilyloxy)cyclohexane-1,2-dicarboxylate

Product 1

HCID 58282618(1R,2R,4R)-2-(tert-butoxycarbonyl)-4-(tert-butyldiphenylsilyloxy)cyclohexanecarboxylic acidYield 63%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

A solution of compound 7 (4.2 mmol) and LiOH (16.8 mmol) in THF/H2O 1/1 (40 mL) was stirred at room temperature for 16 hrs. The reaction mixture was neutralized with 1N HCl to pH 2, and then extracted with DCM (100 mL). Organics were concentrated under reduced pressure and purified by chromatography on silica gel (Cyclohexane/EtOAc) to yield compound 8 as pale yellow oil in 63% yield.

Workup

  1. extractionextracted with DCM (100 mL)
  2. concentrationOrganics were concentrated under reduced pressure
  3. custompurified by chromatography on silica gel (Cyclohexane/EtOAc)

Sources & evidence

ORD record
ord-37184622fae6465b8af571bd9636471e
Source dataset
uspto-grants-2016_05
Patent number
US09353100B2

Reaction notes

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