Acetic Acid → HCID 72524905, compound

HRID 1992751Notes

Reaction equation

[OH:1][CH:2]1[CH2:6][NH:5][CH:4]([CH2:7][N:8]([CH2:24][C:25]([CH3:33])=[CH:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:9]([C:11]2[CH:21]=[C:20]([O:22][CH3:23])[C:14]3[O:15][C:16]([CH3:19])([CH3:18])[O:17][C:13]=3[CH:12]=2)=[O:10])[CH2:3]1.[O:34]1[CH2:39][CH2:38][C:37](=O)[CH2:36][CH2:35]1.C(O)(=O)C.C([BH3-])#N.[Na+].Cl>>[OH:1][CH:2]1[CH2:6][N:5]([CH:37]2[CH2:38][CH2:39][O:34][CH2:35][CH2:36]2)[CH:4]([CH2:7][N:8]([CH2:24][C:25]([CH3:33])=[CH:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:9]([C:11]2[CH:21]=[C:20]([O:22][CH3:23])[C:14]3[O:15][C:16]([CH3:19])([CH3:18])[O:17][C:13]=3[CH:12]=2)=[O:10])[CH2:3]1

Participants

Reactant 5

HCID 176Acetic Acid

HCID 313Hydrochloric Acid

HCID 121599Tetrahydro-4H-pyran-4-one

HCID 5003444Sodium cyanoborohydride

HCID 72524903HCID 72524903, compound

Product 1

HCID 72524905HCID 72524905, compoundYield 69.2%

Procedure

Experimental condition analogous to Example 14 were used with 7-methoxy-2,2-dimethyl-benzo[1,3]dioxole-5-carboxylic acid (4-hydroxy-pyrrolidin-2-ylmethyl)-(2-methyl-3-phenyl-allyl)-amide 0.16 g (0.35 mmol), tetrahydro-4H-pyrane-4-one 0.042 g (0.42 mmol), acetic acid 0.03 ml (0.53 mmol) and sodium cyanoborohydride 0.026 g (0. 42 mmol). After transforming the free base to HCl salt, 130 mg of white solid was obtained. Yield: 65%.

Sources & evidence

ORD record: ord-1a4bbbb67ab44894a2e5e5ba76ecc663
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07649011B2

Reaction notes

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