Pyrrolidine → HCID 59681786, compound

HRID 1394174Notes

Reaction equation

HRID 1394174 reaction equation
[NH2:1][C:2]1[C:3]([C:7]2[N:8]([C:16]3[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=3)[CH:19]=O)[C:9]3[CH:14]=[CH:13][N:12]=[CH:11][C:10]=3[N:15]=2)=[N:4][O:5][N:6]=1.[NH:24]1[CH2:28][CH2:27][CH2:26][CH2:25]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.CO>[N:24]1([CH2:19][C:18]2[CH:17]=[C:16]([N:8]3[C:9]4[CH:14]=[CH:13][N:12]=[CH:11][C:10]=4[N:15]=[C:7]3[C:3]3[C:2]([NH2:1])=[N:6][O:5][N:4]=3)[CH:23]=[CH:22][CH:21]=2)[CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

6

Reactant 3

HCID 31268PyrrolidineHCID 5049666Sodium triacetoxyborohydrideHCID 86600487HCID 86600487, compound

Product 1

HCID 59681786HCID 59681786, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 887MethanolSolvent

Procedure

The product of Step 1 was stirred in 1,2-dichloroethane, and treated with pyrrolidine (27 uL, 0.326 mmol) and stirred for 15 minutes at room temperature. The reaction was then treated with sodium triacetoxyborohydride (34 mg, 0.164 mmol) and stirred at room temperature for 16 hours. The reaction was diluted with methanol and applied to a Mega Bond Elute SCX ion exchange column, eluting sequentially with water, methanol and finally 0.880 ammonia:methanol (1:9). The residue was purified using silica gel chromatography eluting with a mixture of 0.880 ammonia:methanol:dichloromethane (1:9:90) to afford the compound (20 mg, 34%); MS (ES+), m/e 362 [M+H]+.

Workup

  1. stirringstirred at room temperature for 16 hours
  2. washElute SCX ion exchange column
  3. washeluting sequentially with water, methanol and finally 0.880 ammonia:methanol (1:9)
  4. customThe residue was purified
  5. washeluting with a mixture of 0.880 ammonia:methanol:dichloromethane (1:9:90)

Sources & evidence

ORD record
ord-8e8abc91a2b0452890e63193f860fa3a
Source dataset
uspto-grants-2008_03
Patent number
US07348339B2

Reaction notes

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