2-Oxazolidinone → (R)-2-((R)-(3-(cyclohexylmethoxy)phenyl)(trimethylsilyloxy)methyl)butan-1-ol

HRID 875522Notes

Reaction equation

O1CCNC1=O.C([C@@H]1COC(=O)N1[C:20](=[O:44])[C@H:21]([C@H:24]([C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([O:36][CH2:37][CH:38]2[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]2)[CH:31]=1)[O:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[CH2:22][CH3:23])C1C=CC=CC=1>>[CH:38]1([CH2:37][O:36][C:32]2[CH:31]=[C:30]([C@H:24]([O:25][Si:26]([CH3:29])([CH3:27])[CH3:28])[C@H:21]([CH2:22][CH3:23])[CH2:20][OH:44])[CH:35]=[CH:34][CH:33]=2)[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43]1

Participants

Reactant 2

HCID 739492-Oxazolidinone

HCID 67317326(R)-4-benzyl-3-((S)-2-((R)-(3-(cyclohexylmethoxy)phenyl)(trimethylsilyloxy)methyl)butanoyl)-oxazolidin-2-one

Product 1

HCID 67317220(R)-2-((R)-(3-(cyclohexylmethoxy)phenyl)(trimethylsilyloxy)methyl)butan-1-ol

Procedure

Oxazolidinone cleavage of (R)-4-benzyl-3-((S)-2-((R)-(3-(cyclohexylmethoxy)phenyl)(trimethylsilyloxy)methyl)butanoyl)oxazolidin-2-one following the method described in Example 45 gave (R)-2-((R)-(3-(cyclohexylmethoxy)phenyl)-(trimethylsilyloxy)methyl)butan-1-ol as colorless oil. Yield (0.273 g, 21%). 1H NMR (400 MHz, DMSO-d6) δ 7.17 (t, J=7.6 Hz, 1H), 6.73-6.80 (m, 3H), 4.64 (d, J=6.5 Hz, 1H), 4.19 (t, J=5.1 Hz, 1H), 3.41-3.47 (m, 1H), 3.32-3.37 (m, 1H), 1.58-1.79 (m, 6H), 1.48 (m, 1H), 0.99-1.26 (m, 7H), 0.76 (t, J=7.6 Hz, 3H), −0.06 (s, 9H).

Sources & evidence

ORD record: ord-ab8fb89019224ab6b5f83930a579dccb
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08981153B2

Reaction notes

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