Aluminium lithium hydride → HCID 58109290, compound

HRID 2037457Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@:8]2([CH2:27][CH2:28][CH2:29][OH:30])[O:13][C:12](=[O:14])[N:11]([C@H:15]([C:17]3[CH:26]=[CH:25][C:20]([C:21](OC)=[O:22])=[CH:19][CH:18]=3)[CH3:16])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@:8]2([CH2:27][CH2:28][CH2:29][OH:30])[O:13][C:12](=[O:14])[N:11]([C@H:15]([C:17]3[CH:18]=[CH:19][C:20]([CH2:21][OH:22])=[CH:25][CH:26]=3)[CH3:16])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Methyl 4-((S)-1-((R)-6-(4-fluorophenyl)-6-(3-hydroxypropyl)-2-oxo-1,3-oxazinan-3-yl)ethyl)benzoate (10 mg, 0.024 mmol) was dissolved in dry THF (4 mL) and cooled to 0° C. LiAlH4 (2 mg, excess) was added slowly. After 10 min, the mixture was warmed to rt and stirred for 2 h. LC-MS found reaction completed. The mixture was quenched with water, diluted with EtOAc (5 mL), washed with 1% aq HCl (2 mL). After concentration, the residue was purified by prep HPLC to afford (R)-6-(4-fluorophenyl)-3-((S)-1-(4-(hydroxymethyl)phenyl)ethyl)-6-(3-hydroxypropyl)-1,3-oxazinan-2-one (3.0 mg, 32%). LC-MS Method 1 tR=1.2 min, m/z=410 (M+Na); 1H NMR (CDCl3) 7.23 (m, 2H), 7.14 (d, 2H), 7.03 (q, 2H), 6.95 (t, 2H), 5.66 (m, 1H), 4.61 (s, 2H), 3.59 (t, 2H), 1.53 (d, 3H).

Workup

temperaturethe mixture was warmed to rt
customreaction
customThe mixture was quenched with water
additiondiluted with EtOAc (5 mL)
washwashed with 1% aq HCl (2 mL)
concentrationAfter concentration
customthe residue was purified by prep HPLC

Sources & evidence

ORD record: ord-c4c8d4ae2be64bfa96dc9ca6f911a96a
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575156B2

Reaction notes

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