Triethylamine → Ammonium hydroxide methanol

HRID 1044573Notes

Reaction equation

HRID 1044573 reaction equation
Cl.[NH2:2][C@@H:3]1[CH2:7][CH2:6][C@@:5]([C:11]([N:13]2[CH2:18][CH2:17][C:16]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)([OH:19])[CH2:15][CH2:14]2)=[O:12])([CH:8]([CH3:10])[CH3:9])[CH2:4]1.[CH3:26][O:27][CH:28]1[C:33](=O)[CH2:32][CH2:31][O:30][CH2:29]1.C([N:37](CC)CC)C.[C:42](O[BH-](OC(=O)C)OC(=O)C)(=[O:44])C.[Na+]>C(Cl)Cl>[NH4+:2].[OH-:12].[NH4+:37].[OH-:27].[CH3:42][OH:44].[CH:8]([C@:5]1([C:11]([N:13]2[CH2:14][CH2:15][C:16]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)([OH:19])[CH2:17][CH2:18]2)=[O:12])[CH2:6][CH2:7][C@@H:3]([NH:2][CH:33]2[CH2:32][CH2:31][O:30][CH2:29][CH:28]2[O:27][CH3:26])[CH2:4]1)([CH3:9])[CH3:10]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 235336103-Methoxyoxan-4-oneHCID 68936202HCID 68936202, compound

Product 3

HCID 14923Ammonium HydroxideHCID 11568482HCID 11568482, compoundHCID 21894508Ammonium hydroxide methanolYield 1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-{[(1S,3R)-3-amino-1-isopropylcyclopentyl]carbonyl}-4-phenylpiperidin-4-ol hydrochloride (50 mg, 0.1 mmol), 3-methoxytetrahydro-4H-pyran-4-one (53 mg, 0.41 mmol), and triethylamine (0.066 mL, 0.48 mmol) in methylene chloride (2 mL) was added sodium triacetoxyborohydride (0.087 g, 0.41 mmol). After being stirred overnight at room temperature, the reaction was quenched with a saturated NaHCO3 solution. The resulting solution was extracted with methylene chloride three times. The combined extracts were dried (MgSO4), filtered, and concentrated. Purification by flash chromatography on silica gel (0-20% B over 17 min. Bottle A=1% NH4OH/2% MeOH/EtOAc, Bottle B=1% NH4OH/MeOH) afforded the desired product. MS calculated for C26H40N2O4: (M+H) 445; found 445.2.

Workup

  1. customthe reaction was quenched with a saturated NaHCO3 solution
  2. extractionThe resulting solution was extracted with methylene chloride three times
  3. dry with materialThe combined extracts were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by flash chromatography on silica gel (0-20% B over 17 min

Sources & evidence

ORD record
ord-749c760b3eee411d9c6448491517bf90
Source dataset
uspto-grants-2013_10
Patent number
US08563582B2

Reaction notes

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