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

HRID 426067Notes

Reaction equation

HRID 426067 reaction equation
CC1(C)[N:6](C(OC(C)(C)C)=O)[C@@H:5]([CH2:14][C@H:15]2[CH2:20][CH2:19][CH2:18][O:17][CH2:16]2)[CH2:4][O:3]1>C(O)(C(F)(F)F)=O.O>[NH2:6][C@@H:5]([CH2:14][C@H:15]1[CH2:20][CH2:19][CH2:18][O:17][CH2:16]1)[CH2:4][OH:3]

Participants

4

Reactant 1

HCID 58011520(S)-tert-Butyl 2,2-dimethyl-4-(((R)-tetrahydro-2H-pyran-3-yl)methyl)oxazolidine-3-carboxylate

Product 1

HCID 59364346(S)-2-amino-3-((R)-tetrahydro-2H-pyran-3-yl)propan-1-olYield 293.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

(S)-tert-butyl 2,2-dimethyl-4-(((R)-tetrahydro-2H-pyran-3-yl)methyl)oxazolidine-3-carboxylate (32 g) was dissolved in a mixture of TFA (160 mL) and water (160 mL). The mixture was stirred at room temperature for 10 min. The mixture was then concentrated in vacuo to give the crude product (50 g), which was used for the next step without further purification.

Workup

  1. concentrationThe mixture was then concentrated in vacuo

Sources & evidence

ORD record
ord-5338353b77584fde9bf9a16e29e649c3
Source dataset
uspto-grants-2012_01
Patent number
US08106221B2

Reaction notes

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