Hydrochloric Acid → HCID 59569764, compound

HRID 2070954Notes

Reaction equation

HRID 2070954 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:21]=[C:22]([CH:24]([CH3:26])[CH3:25])[CH:23]=1)[CH2:12][NH:13]C(=O)OC(C)(C)C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>CO>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:12][NH2:13])[CH:21]=[C:22]([CH:24]([CH3:26])[CH3:25])[CH:23]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68671142HCID 68671142, compound

Product 1

HCID 59569764HCID 59569764, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of tert-butyl 3-(benzyloxy)-5-isopropylbenzylcarbamate and 15.0 mL of 1.25 M HCl in MeOH was stirred at r.t. for 3.5 h. The solution was concentrated, and saturated NaHCO3 was added to a pH=7-8. The aqueous layer was extracted with the extract of (40 mL CHCl3: 5 mL MeOH: 5 mL H2O) (2×). The combined extracts were dried over Na2SO4, filtered, and concentrated to give 221 mg of crude (3-(benzyloxy)-5-isopropylphenyl)methanamine which was used for the next reaction without further purification.

Workup

  1. concentrationThe solution was concentrated
  2. additionsaturated NaHCO3 was added to a pH=7-8
  3. extractionThe aqueous layer was extracted with the
  4. extractionextract of (40 mL CHCl3: 5 mL MeOH: 5 mL H2O) (2×)
  5. dry with materialThe combined extracts were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2fd49cb25ef64f0da55b9331ae69e813
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

Loading…