Trifluoroacetic acid → HCID 67071750, compound

HRID 1260569Notes

Reaction equation

HRID 1260569 reaction equation
[CH2:1]([O:8][C:9]1[CH:33]=[CH:32][C:12]([O:13][C:14]2[CH:31]=[CH:30][C:17]([O:18][CH2:19][CH:20]([NH:22]C(=O)OC(C)(C)C)[CH3:21])=[CH:16][CH:15]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>>[CH2:1]([O:8][C:9]1[CH:33]=[CH:32][C:12]([O:13][C:14]2[CH:31]=[CH:30][C:17]([O:18][CH2:19][C@@H:20]([NH2:22])[CH3:21])=[CH:16][CH:15]=2)=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86761885HCID 86761885, compound

Product 1

HCID 67071750HCID 67071750, compound

Procedure

tert-Butyl {2-[4-(4-benzyloxyphenoxy)phenoxy]-1-methylethyl}carbamate (837 mg, 1.86 mmol) was treated with 90 percent strength trifluoroacetic acid. The trifluoroacetic acid was distilled off and the aqueous phase was freeze dried. Chromatography was performed on a chiral column (ChiralpakAD-H/91, 250 4.6 mm, eluent: heptane/ethanol=3:1+0.1% DEA) for enantiomer separation (S)-2-[4-(4-Benzyloxyphenoxy)phenoxy]-1-methylethylamine (RF: 11.667 min.), Yield: 230 mg (35%), M+H+: 350.19, (R)-2-[4-(4-benzyloxyphenoxy)phenoxy]-1-methylethylamine (RF: 13.122 min.), Yield: 226 mg (35%), M+H+: 350.19.

Workup

  1. distillationThe trifluoroacetic acid was distilled off
  2. customdried
  3. customChromatography was performed on a chiral column (ChiralpakAD-H/91, 250 4.6 mm, eluent: heptane/ethanol=3:1+0.1% DEA) for enantiomer separation (S)-2-[4-(4-Benzyloxyphenoxy)phenoxy]-1-methylethylamine (RF: 11.667 min.), Yield: 230 mg (35%), M+H+
  4. custom350.19, (R)-2-[4-(4-benzyloxyphenoxy)phenoxy]-1-methylethylamine (RF: 13.122 min.), Yield: 226 mg (35%), M+H+

Sources & evidence

ORD record
ord-31b53bc2903741cba09325e4a83e8ec5
Source dataset
uspto-grants-2013_06
Patent number
US08470841B2

Reaction notes

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