Hydrochloric Acid → (1S,2R,4R)-1,2-bis((7,7-dimethyl-2-morpholinobicyclo[2.2.1]heptan-1-yl)methyl)disulfane hydrochloride

HRID 537005Notes

Reaction equation

HRID 537005 reaction equation
[CH3:1][C:2]1([CH3:34])[C@@H:6]2[CH2:7][CH2:8][C@@:3]1([CH2:15][S:16][S:17][CH2:18][C:19]13[C:25]([CH3:27])([CH3:26])[CH:22]([CH2:23][CH2:24]1)[CH2:21][CH:20]3[N:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1)[C@H:4]([N:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1)[CH2:5]2.[ClH:35]>CC(O)C.CCCCCCC>[ClH:35].[CH3:26][C:25]1([CH3:27])[C@@H:22]2[CH2:23][CH2:24][C@@:19]1([CH2:18][S:17][S:16][CH2:15][C:3]13[C:2]([CH3:1])([CH3:34])[CH:6]([CH2:7][CH2:8]1)[CH2:5][CH:4]3[N:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1)[C@H:20]([N:28]1[CH2:29][CH2:30][O:31][CH2:32][CH2:33]1)[CH2:21]2

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86687332(1S,2R,4R)-1,2-bis((7,7-dimethyl-2-morpholinobicyclo[2.2.1]heptan-1-yl)methyl)disulfane

Product 1

HCID 86687331(1S,2R,4R)-1,2-bis((7,7-dimethyl-2-morpholinobicyclo[2.2.1]heptan-1-yl)methyl)disulfane hydrochloride

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolvent2×HCID 8900HeptaneSolvent

Procedure

To a solution (1S,2R,4R)-1,2-bis((7,7-dimethyl-2-morpholinobicyclo[2.2.1]heptan-1-yl)methyl)disulfane (IIIa) (111 mg, 0.22 mmol) in IPA (1 mL) and n-heptane (2 mL) was added a solution of HCl in IPA (1 mL, 4.9 mmol). The resulting mixture was concentrated in vacuo to give the title product (1S,2R,4R)-1,2-bis((7,7-dimethyl-2-morpholinobicyclo[2.2.1]heptan-1-yl)methyl)disulfane hydrochloride (IIIb) as a white powder.

Workup

  1. concentrationThe resulting mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-6196fcd22a1541388311dfa2f1e773bc
Source dataset
uspto-grants-2014_10
Patent number
US08859765B2

Reaction notes

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