Benzyl ((3R,4R)-4-methyl-5-oxotetrahydrofuran-3-yl)carbamate → benzyl {(1R,2R)-1-hydroxymethyl-2-[3-methyl-4-(3-oxo-morpholin-4-yl)-phenylcarbamoyl]-propyl}-carbamate

HRID 1434524Notes

Reaction equation

HRID 1434524 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][C:9]2=[O:14])=[C:4]([CH3:15])[CH:3]=1.[CH3:16][C@H:17]1[C:21](=[O:22])[O:20][CH2:19][C@@H:18]1[NH:23][C:24](=[O:33])[O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C[Al](C)C>C1COCC1>[OH:20][CH2:19][C@H:18]([NH:23][C:24](=[O:33])[O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C@H:17]([C:21](=[O:22])[NH:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][C:9]2=[O:14])=[C:4]([CH3:15])[CH:3]=1)[CH3:16]

Participants

5

Reactant 3

HCID 13108321Benzyl ((3R,4R)-4-methyl-5-oxotetrahydrofuran-3-yl)carbamateHCID 16682925TrimethylaluminumHCID 231052884-(4-Amino-2-methylphenyl)morpholin-3-one

Product 1

HCID 86605956benzyl {(1R,2R)-1-hydroxymethyl-2-[3-methyl-4-(3-oxo-morpholin-4-yl)-phenylcarbamoyl]-propyl}-carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Prepared analogously to Example 2b from 4-(4-amino-2-methyl-phenyl)-morpholin-3-one and benzyl [(3R,4R)-4-methyl-5-oxo-tetrahydrofuran-3-yl]-carbamate with trimethylaluminium in THF and subsequent purification by reversed-phase chromatography.

Sources & evidence

ORD record
ord-6ac37ebc32fa4e0ea1ad7fe0606d30f4
Source dataset
uspto-grants-2009_11
Patent number
US07615549B2

Reaction notes

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