3-Azido-N-cyclopropyl-2-hydroxyhexanamide → 3-Amino-N-cyclopropyl-2-hydroxyhexanamide

HRID 540979Notes

Reaction equation

[N:1]([CH:4]([CH2:13][CH2:14][CH3:15])[CH:5]([OH:12])[C:6]([NH:8][CH:9]1[CH2:11][CH2:10]1)=[O:7])=[N+]=[N-]>[Pd].CO>[NH2:1][CH:4]([CH2:13][CH2:14][CH3:15])[CH:5]([OH:12])[C:6]([NH:8][CH:9]1[CH2:10][CH2:11]1)=[O:7]

Participants

Conditions

Temperature: 25 °C

Procedure

Compound 40 (15.1 g, 71.3 mmol), Pd/C (1.5 g, 5 wt %, 50% wet) and MeOH (150 mL) was charged to a pressure vessel then purged with nitrogen gas for 5 min. The vessel was sealed, pressurized to 1 bar with nitrogen gas then released three times. The same was repeated with hydrogen gas. After the third purge with hydrogen the vessel was charged with 3 hydrogen at a pressure of 3 bars. The reaction was agitated and a temperature of 25±5° C. was maintained for 14 hours after which time the reaction mixture was filtered through a pad of Celite 545 and the solvent removed to provide crude compound 41 (8.48 g) as a yellow solid. To this material was added acetonitrile (ACN; 150 mL) and the reaction heated to reflux at which time all of the solids dissolved. The mixture was then cooled to 25±5° C. and the white needles formed were collected, washed with cold ACN and dried to provide purified compound 41. 1H NMR (500 MHz, d6-DMSO): 8.05 (br s, 3H), 4.20 (d, J=3.2, 1 H), 3.42-3.34 (m, 1H), 2.71-2.65 (m, 1H), 1.51-1.20 (m, 4H), 1.17 (d, J=6.5 Hz, 1H), 0.83 (t, J=7.6 Hz, 3H), 0.64-0.60 (m, 2H), 0.54-0.49 (m, 2H).

Workup

customthen purged with nitrogen gas for 5 min
customThe vessel was sealed
customAfter the third purge with hydrogen the vessel
additionwas charged with 3 hydrogen at a pressure of 3 bars
filtrationwas filtered through a pad of Celite 545
customthe solvent removed

Sources & evidence

ORD record: ord-335640a9bf5f455dae931c3e175b9abf
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871904B2

Reaction notes

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