tert-Butanol → HCID 67198373, compound

HRID 225466Notes

Reaction equation

HRID 225466 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.C(OCC)(=O)C.Cl.Cl>[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 21477582HCID 21477582, compoundHCID 67200022HCID 67200022, compound

Product 1

HCID 67198373HCID 67198373, compound

Reagents, catalysts & solvents 2

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

Procedure

A solution of tert-butanol of N-methylmorpholine-N-oxide and osmium tetroxide was added to a mixture of 1-benzyl-4-methyleneazepane hydrochloride and THF-water and stirred at room temperature for 24 hours. Then the reaction solution was processed with 4M hydrochloric acid (HCl)-ethyl acetate (EtOAc) solution to give 1-benzyl-4-(hydroxymethyl)azepane-4-ol hydrochloride. 10% palladium carbon was added to a solution of EtOH of the obtained 1-benzyl-4-(hydroxymethyl)azepane-4-ol hydrochloride and stirred for six hours at room temperature under the hydrogen atmosphere to give 4-(hydroxymethyl)azepane-4-ol hydrochloride.

Sources & evidence

ORD record
ord-dc4890eee1964f80afb3f7e1de7ba650
Source dataset
uspto-grants-2009_07
Patent number
US07557112B2

Reaction notes

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