Benzaldehyde → (+/-)-cis-N-benzyl-4,5,7,7a,8,9,10,10a-octahydrodipyrrolo[3,4-c:3',2',1'-ij]quinolin-2-amine

HRID 1836593Notes

Reaction equation

HRID 1836593 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:9][C:10]1[CH:11]=[C:12]2[C:17]3=[C:18]([CH2:20][CH2:21][N:16]3[CH2:15][C@@H:14]3[CH2:22][N:23](C(OC(C)(C)C)=O)[CH2:24][C@H:13]23)[CH:19]=1>>[CH2:1]([NH:9][C:10]1[CH:11]=[C:12]2[C:17]3=[C:18]([CH2:20][CH2:21][N:16]3[CH2:15][C@@H:14]3[CH2:22][NH:23][CH2:24][C@H:13]23)[CH:19]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 240BenzaldehydeHCID 131724549(+/-)-cis tert-butyl 2-amino-4,5,7a,8,10,10a-hexahydrodipyrrolo[3,4-c:3',2',1'-ij]quinoline-9(7H)-carboxylate

Product 1

HCID 68523002(+/-)-cis-N-benzyl-4,5,7,7a,8,9,10,10a-octahydrodipyrrolo[3,4-c:3',2',1'-ij]quinolin-2-amine

Procedure

Using benzaldehyde and following the procedures described in EXAMPLE 76, (±)-cis tert-butyl 2-amino-4,5,7a,8,10,10a-hexahydrodipyrrolo[3,4-c:3′,2′,1′-ij]quinoline-9(7H)-carboxylate was converted into (±)-cis-N-benzyl-4,5,7,7a,8,9,10,10a-octahydrodipyrrolo[3,4-c:3′,2′,1′-ij]quinolin-2-amine, bis-trifluoroacetic acid salt, after HPLC purification (C18 reverse phase column, elution with a H2O/CH3CN gradient with 0.5% TFA). This material was free-based with aq ammonium hydroxide, extracted with chloroform, washed with brine, dried (K2CO3) and concentrated to the title compound of EXAMPLE 118 as the free base. LRMS (ES)+: 306.3 (M+H)+.

Workup

  1. customafter HPLC purification (C18
  2. washphase column, elution with a H2O/CH3CN gradient with 0.5% TFA)
  3. extractionextracted with chloroform
  4. washwashed with brine
  5. dry with materialdried (K2CO3)
  6. concentrationconcentrated to the title compound of EXAMPLE 118 as the free base

Sources & evidence

ORD record
ord-6cbf85d061fc471bbf144ddfed7a2256
Source dataset
uspto-grants-2004_08
Patent number
US06777406B2

Reaction notes

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