Trifluoroacetic acid → (S)-6-{[(4-Methoxybenzyl)(tetrahydropyran-4-ylmethyl)amino]methyl}-1,2,3,4-tetrahydronaphthalen-2-ylamine

HRID 77420Notes

Reaction equation

HRID 77420 reaction equation
C(OC(=O)[NH:7][C@H:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:18](=O)[N:19]([CH2:27][C:28]3[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=3)[CH2:20][CH:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)[CH:14]=2)[CH2:9]1)(C)(C)C.FC(F)(F)C(O)=O.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[CH3:35][O:34][C:31]1[CH:30]=[CH:29][C:28]([CH2:27][N:19]([CH2:18][C:13]2[CH:14]=[C:15]3[C:10](=[CH:11][CH:12]=2)[CH2:9][C@@H:8]([NH2:7])[CH2:17][CH2:16]3)[CH2:20][CH:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 66663601{(S)-6-[(4-Methoxybenzyl)(tetrahydropyran-4-ylmethyl)carbamoyl]-1,2,3,4-tetrahydro-naphthalen-2-yl}carbamic acid tert-butyl ester

Product 1

HCID 66664086(S)-6-{[(4-Methoxybenzyl)(tetrahydropyran-4-ylmethyl)amino]methyl}-1,2,3,4-tetrahydronaphthalen-2-ylamine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of {(S)-6-[(4-methoxybenzyl)(tetrahydropyran-4-ylmethyl)carbamoyl]-1,2,3,4-tetrahydronaphthalen-2-yl}carbamic acid tert-butyl ester (9.90 g) and dichloromethane (30 ml) was admixed cautiously with trifluoroacetic acid (2.2 g). After one hour, the reaction mixture was basified with saturated potassium carbonate solution. The organic phase was removed, dried over sodium sulfate and concentrated. The crude product was taken up in THF (300 ml) and treated according to method H with lithium aluminum hydride (reaction time 4 hours). The product was thus obtained with the molecular weight of 394.56 (C25H34N2O2); MS

Workup

  1. customThe organic phase was removed
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated
  4. additiontreated
  5. customaccording to method H with lithium aluminum hydride (reaction time 4 hours)
  6. customThe product was thus obtained with the molecular weight of 394.56 (C25H34N2O2)

Sources & evidence

ORD record
ord-62883fd1549c4c1db7f2a7c08c8769bf
Source dataset
uspto-grants-2014_09
Patent number
US08841290B2

Reaction notes

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