Sodium Hydroxide → HCID 66702124, compound

HRID 426425Notes

Reaction equation

HRID 426425 reaction equation
[CH:1]1([CH2:7][CH:8]([C:16]([O:18][CH3:19])=[O:17])[CH2:9][C@@H:10](O)S([O-])(=O)=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Na+].[OH-].[Na+].Cl.[NH2:24][C@H:25]1[C:34]([CH2:37][CH3:38])([CH2:35][CH3:36])[C:33]2[CH:32]=[C:31]([OH:39])[CH:30]=[CH:29][C:28]=2[CH2:27][C@@H:26]1[O:40][CH3:41].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CC1OCCC1.CCOC(C)=O>[CH3:19][O:18][C:16](=[O:17])[C@@H:8]([CH2:7][CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[CH2:9][CH2:10][NH:24][C@@H:25]1[C@@H:26]([O:40][CH3:41])[CH2:27][C:28]2[C:33](=[CH:32][C:31]([OH:39])=[CH:30][CH:29]=2)[C:34]1([CH2:37][CH3:38])[CH2:35][CH3:36]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 66674947HCID 66674947, compoundHCID 86631184HCID 86631184, compound

Product 1

HCID 66702124HCID 66702124, compoundYield 101.9%

Reagents, catalysts & solvents 2

HCID 73012-MethyltetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a slurry of sodium (S)-4-cyclohexyl-1-hydroxy-3-methoxycarbonyl-butane-1-sulfonate (158 mg, 0.5 mmol) in 2-MeTHF (2 mL) was added 2N NaOH (0.22 mL, 0.44 mmol). The reaction mixture was stirred for 20 min at which time all of the solids had dissolved. (6S,7S)-7-Amino-8,8-diethyl-6-methoxy-5,6,7,8-tetrahydro-naphthalen-2-ol hydrochloride (100 mg, 0.35 mmol) was added and the mixture was stirred at RT for 30 min. Sodium triacetoxyborohydride (425 mg, 2.0 mmol) was added in 4 portions over 3 h. Thirty minutes after the last addition, EtOAc (15 mL) was added and the mixture was washed with 5% aqueous sodium carbonate (2×5 mL) and saturated sodium chloride (5 mL). The organic layer was dried with Na2SO4 and concentrated to give the title compound (159 mg). (m/z): [M+H]+ calcd for C27H43NO4, 446.33. Found, 446.6.

Workup

  1. dissolutionhad dissolved
  2. stirringthe mixture was stirred at RT for 30 min
  3. additionwas added
  4. washthe mixture was washed with 5% aqueous sodium carbonate (2×5 mL) and saturated sodium chloride (5 mL)
  5. dry with materialThe organic layer was dried with Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e21b3fbdbd43418c8c557e39eaef2403
Source dataset
uspto-grants-2012_01
Patent number
US08106232B2

Reaction notes

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