Trifluoroacetic acid → HCID 9877581, compound

HRID 2308223Notes

Reaction equation

[CH2:1]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:2]1C=CC=CC=1.[N:16]#[C:17][NH2:18].[C:19](O)(C(F)(F)F)=O.BrC#N>>[CH2:9]([O:8][CH:1]1[CH2:2][N:16]([C:17]#[N:18])[CH2:19]1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

Reactant 4

HCID 6422Trifluoroacetic acid

HCID 7657Dibenzyl ether

HCID 9864Cyanamide

HCID 10476Cyanogen Bromide

Product 1

HCID 9877581HCID 9877581, compound

Procedure

Following general procedure 12, to a cold (0° C.), stirred solution of the alcohol (46) (173 mg, 1 equiv.) in DMF (2 mL) was added NaH,(60% in oil, 60 mg, 1.5 equiv.). The suspension was stirred at 0° C. for 30 minutes followed by the addition of the benzyl chloride (230 uL, 2 equiv.). The resulting suspension was poured into H2O and extracted with Et2O (3×). The combined organic extracts were washed with H2O and brine, dried (MgSO4) and concentrated under reduced pressure. The residue was purified by flash chromatography (gradient elution: 10% EtOAc in hexane to 25% EtOAc in hexane) to afford the desired benzyl ether. The N-Boc group of the benzyl ether 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: 10% EtOAc in hexane to 33% EtOAc in hexane) to afford the desired product 3-(benzyloxy)-1-cyanoazetidine (59).

Workup

customThe crude material was purified by flash chromatography (gradient elution: 10% EtOAc in hexane to 33% EtOAc in hexane)

Sources & evidence

ORD record: ord-f2cd879a3262466ba3640bc031969775
Source dataset: uspto-grants-2004_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06835727B2

Reaction notes

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