Hydrochloric Acid → Tert-butyl (1-(2-(1,2-dihydroxyethyl)quinolin-8-yl)piperidin-4-yl)methylcarbamate

HRID 1041959Notes

Reaction equation

HRID 1041959 reaction equation
CC1(C)[O:6][CH:5]([C:7]2[CH:16]=[CH:15][C:14]3[C:9](=[C:10]([N:17]4[CH2:22][CH2:21][CH:20]([CH2:23][NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:19][CH2:18]4)[CH:11]=[CH:12][CH:13]=3)[N:8]=2)[CH2:4][O:3]1.Cl>C1COCC1.CCOC(C)=O.C([O-])(O)=O.[Na+]>[OH:6][CH:5]([C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[C:10]([N:17]3[CH2:18][CH2:19][CH:20]([CH2:23][NH:24][C:25](=[O:31])[O:26][C:27]([CH3:29])([CH3:28])[CH3:30])[CH2:21][CH2:22]3)[CH:11]=[CH:12][CH:13]=2)[N:8]=1)[CH2:4][OH:3]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 86654343Tert-butyl (1-(2-(2,2-dimethyl-1,3-dioxolan-4-yl)quinolin-8-yl)piperidin-4-yl)methylcarbamate

Product 1

HCID 86654344Tert-butyl (1-(2-(1,2-dihydroxyethyl)quinolin-8-yl)piperidin-4-yl)methylcarbamate

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To tert-butyl (1-(2-(2,2-dimethyl-1,3-dioxo lan-4-yl)quinolin-8-yl)piperidin-4-yl)methylcarbamate (81 mg, 0.18 mmol) in THF (3 mL) was added HCl (20 mg, 0.55 mmol) (6M). The reaction was stirred for 3 hours at ambient temperature and then diluted with EtOAc (10 mL) and saturated NaHCO3 (5 mL). The phases were separated, and the organic layer was dried and concentrated to give crude product.

Workup

  1. customThe phases were separated
  2. customthe organic layer was dried
  3. concentrationconcentrated
  4. customto give crude product

Sources & evidence

ORD record
ord-a83690f905294084aa3e89006c90488d
Source dataset
uspto-grants-2013_10
Patent number
US08557809B2

Reaction notes

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