tert-Butanol → HCID 67198373, compound

HRID 550784Notes

Reaction equation

HRID 550784 reaction equation
[C:1]([OH:5])([CH3:4])([CH3:3])[CH3:2].C[N+]1([O-])CC[O:10]CC1.[ClH:14].[CH2:15]([N:22]1[CH2:28][CH2:27]CC(=C)C[CH2:23]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.Cl.CCOC(C)=O>[Os](=O)(=O)(=O)=O.C1COCC1.O>[ClH:14].[CH2:15]([N:22]1[CH2:28][CH2:27][CH2:3][C:1]([CH2:4][OH:10])([OH:5])[CH2:2][CH2:23]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 6386tert-ButanolHCID 82029Methyl morpholine oxideHCID 21866389Hydrogen chloride-ethyl acetateHCID 67200022HCID 67200022, compound

Product 1

HCID 67198373HCID 67198373, compound

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 21881883Oxolane--water (1/1)Solvent

Procedure

A tert-butanol solution of N-methylmorpholine-N-oxide and osmium tetraoxide was added to a mixture of 1-benzyl-4-methyleneazepane hydrochloride and THF-water, and the resultant solution was stirred at ambient temperature for 24 hours and then treated with 4M HCl-EtOAc solution to yield 1-benzyl-4-(hydroxymethyl)azepan-4-ol hydrochloride. To an EtOH solution of 1-benzyl-4-(hydroxymethyl)azepan-4-ol hydrochloride obtained was added 10% palladium on activated carbon, and the suspension was stirred under hydrogen atmosphere at ambient temperature for 6 hours to yield 4-(hydroxymethyl)azepan-4-ol hydrochloride.

Sources & evidence

ORD record
ord-50c1de284acf4d4ca256fccda7c478e1
Source dataset
uspto-grants-2011_05
Patent number
US07947690B2

Reaction notes

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