Methanol → HCID 20672303, compound

A solution of 156 mg (0.36 mmol) of (3-(1-t-butoxycarbonyl-piperidin-4-yl)-2-(R)methylpropyl)-4-(S)-benzyloxazolidin-2-one (from EXAMPLE 99, Step A) in 3 mL of THF at O° C. was treated with 0.03 mL (0.73 mmol) of MeOH followed by 16 mg (0.73 mmol) of lithium borohydride. The cooling bath was removed, the mixture was warmed to rt and stirred for 3 h. The reaction was quenched with H2O and sat'd sodium potassium tartrate. The quenched mixture was diluted with CH2Cl2 and stirred for 1 h, then extracted 3× with CH2Cl2. The combined organic layers were washed with sat'd NaCl, dried over Na2SO4, filtered and the filtrate concentrated. Purification by silica gel column chomatography with 0-25% EtOAc/hexanes (v/v) provided 72 mg (77%) of the title compound: 1H NMR (500 MHz) δ 0.92 (d, J=6.8,33H). 1.01-1.12 (3H), 1.27-1.33 (m, 1H), 1.45 (s, 9H), 1.46-1.50 (m, 1H), 1.61-1.75 (4H), 2.69 (bq, 2H), 3.41 (dd, J=3.9,6.6 Hz, 1H). 3.49 (dd, J=4.8, 5.7, 1H). 4.07 (bd, 2H).

1. customThe cooling bath was removed
2. customThe reaction was quenched with H2O
3. additionThe quenched mixture was diluted with CH2Cl2
4. stirringstirred for 1 h
5. extractionextracted 3× with CH2Cl2
6. washThe combined organic layers were washed with sat'd NaCl
7. dry with materialdried over Na2SO4
8. filtrationfiltered
9. concentrationthe filtrate concentrated
10. customPurification by silica gel column chomatography with 0-25% EtOAc/hexanes (v/v)

ORD record

ord-9fcbe803dab942a9a00f729de682e410

Source dataset

uspto-grants-2001_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06265434B1