Triethylamine → HCID 66702020, compound

HRID 870278Notes

Reaction equation

HRID 870278 reaction equation
Cl.[NH2:2][C@H:3]1[C:12]([CH2:15][CH3:16])([CH2:13][CH3:14])[C:11]2[CH:10]=[C:9]([OH:17])[CH:8]=[CH:7][C:6]=2[CH2:5][C@@H:4]1[O:18][CH3:19].C[O:21][C:22](=[O:34])[C@H:23]([CH2:27][CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1)[CH2:24][CH:25]=O.C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.CCOC(C)=O>[CH:28]1([CH2:27][C@H:23]([CH2:24][CH2:25][NH:2][C@@H:3]2[C@@H:4]([O:18][CH3:19])[CH2:5][C:6]3[C:11](=[CH:10][C:9]([OH:17])=[CH:8][CH:7]=3)[C:12]2([CH2:15][CH3:16])[CH2:13][CH3:14])[C:22]([OH:34])=[O:21])[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydride2×HCID 66674947HCID 66674947, compoundHCID 86631187HCID 86631187, compound2×

Product 1

HCID 66702020HCID 66702020, compoundYield 125.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

(6S,7S)-7-Amino-8,8-diethyl-6-methoxy-5,6,7,8-tetrahydro-naphthalen-2-ol hydrochloride salt (100 mg, 0.35 mmol), (R)-2-cyclohexylmethyl-4-oxo-butyric acid methyl ester (90 mg, 0.42 mmol) and triethylamine (35 mg, 0.035 mmol) were dissolved in dichloromethane (2.0 mL) and stirred at room temperature for 30 min. Sodium triacetoxyborohydride (1.03 g, 4.85 mmol) was added and the reaction was monitored by HPLC. After 3 h, additional (R)-2-cyclohexylmethyl-4-oxo-butyric acid methyl ester (20 mg, 0.1 mmol) and sodium triacetoxyborohydride (30 mg, 0.14 mmol) were added. 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 (190 mg). (m/z): [M+H]+ calcd for C27H43NO4, 446.33; found, 446.6.

Workup

  1. waitAfter 3 h
  2. additionwas added
  3. washthe mixture was washed with 5% aqueous sodium carbonate (2×5 mL) and saturated sodium chloride (5 mL)
  4. dry with materialThe organic layer was dried with Na2SO4) and
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6e510cc1e6f9435a90d9986824ed6747
Source dataset
uspto-grants-2015_03
Patent number
US08969370B2

Reaction notes

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