(S)-tert-Butyl 2,2-dimethyl-4-(((R)-tetrahydro-2H-pyran-3-yl)methyl)oxazolidine-3-carboxylate → tert-Butyl ((S)-1-hydroxy-3-((R)-tetrahydro-2H-pyran-3-yl)propan-2-yl)carbamate

HRID 451855Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][C@H:14]2[CH2:19][CH2:18][CH2:17][O:16][CH2:15]2)[CH2:11][O:10]C1(C)C)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CC(O)=O>[OH:10][CH2:11][C@@H:12]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])[CH2:13][C@H:14]1[CH2:19][CH2:18][CH2:17][O:16][CH2:15]1

Participants

Conditions

Temperature: 50 °C

Procedure

(S)-tert-Butyl-2,2-dimethyl-4-(((R)-tetrahydro-2H-pyran-3-yl)methyl)oxazolidine-3-carboxylate (9 g, 30.1 mmol) was dissolved in 80% CH3CO2H (90 ml). The solution was stirred at 50° C. during 1.5 hr and evaporated to dryness at reduced pressure. The residue was dissolved in Et2O (150 ml) and washed with saturated NaHCO3 (4×100 mL). The organic layer was dried over Na2SO4, filtered, and the solvent removed under reduced pressure to give tert-butyl (S)-1-hydroxy-3-((R)-tetrahydro-2H-pyran-3-yl)propan-2-ylcarbamate (6.2 g, 79.5%) as an oil, which was used in the next step without further purification.

Workup

customevaporated to dryness at reduced pressure
dissolutionThe residue was dissolved in Et2O (150 ml)
washwashed with saturated NaHCO3 (4×100 mL)
dry with materialThe organic layer was dried over Na2SO4
filtrationfiltered
customthe solvent removed under reduced pressure

Sources & evidence

ORD record: ord-bcd026fb947b4652b9b64800e3328217
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08487108B2

Reaction notes

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