Trifluoroacetic acid → HCID 9899272, compound

HRID 2308213Notes

Reaction equation

[CH2:1]([O:8][CH2:9][C:10]1[CH:15]=[CH:14]C=C[CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:16]#[C:17][NH2:18].C(O)(C(F)(F)F)=O.BrC#N>>[CH2:1]([O:8][CH2:9][CH:10]1[CH2:15][CH2:14][N:18]([C:17]#[N:16])[CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 4

HCID 6422Trifluoroacetic acid

HCID 7657Dibenzyl ether

HCID 9864Cyanamide

HCID 10476Cyanogen Bromide

Product 1

HCID 9899272HCID 9899272, compound

Procedure

Following general procedure 12, to a cold (0° C.), stirred solution of the alcohol (26) (188 mg, 1 equiv.) in DMF (9 mL) was added NaH (60% in oil, 56 mg, 1.5 equiv.). The suspension was stirred at 0° C. for 40 minutes followed by the addition of the benzyl chloride (215 uL, 2 equiv.). The suspension was warmed to rt and stirred for 16 h. MeOH was added followed by sat. aq. NH4Cl. The aqueous phase was extracted with EtOAc (3×) and the combined organic extracts were washed with brine, dried (MgSO4) and concentrated under reduced pressure. The residue was purified by flash chromatography (20% EtOAc in hexane) to afford the desired benzyl ether (27). The N-Boc group of the benzyl ether (27) was then converted to the cyanamide (N—CN) following general procedure 3 (i.e. successive treatment with TFA and BrCN). The crude material was purified by flash chromatography (gradient elution: 30% EtOAc in hexane to 50% EtOAc in hexane) to afford the desired product 3-[(benzyloxy)methyl]-1-cyanopyrrolidine (28).

Workup

customThe crude material was purified by flash chromatography (gradient elution: 30% EtOAc in hexane to 50% EtOAc in hexane)

Sources & evidence

ORD record: ord-93cba63612c34f8fb5f862143d5f5f2a
Source dataset: uspto-grants-2004_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06835727B2

Reaction notes

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