Formaldehyde → HCID 66662371, compound

HRID 557950Notes

Reaction equation

C=O.[N:3]1([C:9]2[CH:14]=[CH:13][C:12]([C:15]3([C:18]([N:20]4[CH2:24][CH2:23][C@@:22]5([C:28]6[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=6[C:26](=[O:33])[O:25]5)[CH2:21]4)=[O:19])[CH2:17][CH2:16]3)=[CH:11][CH:10]=2)[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.CO.[C:36](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>>[CH3:36][N:6]1[CH2:7][CH2:8][N:3]([C:9]2[CH:10]=[CH:11][C:12]([C:15]3([C:18]([N:20]4[CH2:24][CH2:23][C@@:22]5([C:28]6[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=6[C:26](=[O:33])[O:25]5)[CH2:21]4)=[O:19])[CH2:17][CH2:16]3)=[CH:13][CH:14]=2)[CH2:4][CH2:5]1

Participants

Reactant 4

HCID 712Formaldehyde

HCID 887Methanol

HCID 5049666Sodium triacetoxyborohydride

HCID 66661956HCID 66661956, compound

Product 1

HCID 66662371HCID 66662371, compound

Procedure

Formaldehyde (10.0 mg, 0.000333 mol) was added to a solution of (1R)-1′-{[1-(4-piperazin-1-ylphenyl)cyclopropyl]carbonyl}-3H-spiro[2-benzofuran-1,3′-pyrrolidin]-3-one (0.13 g, 0.00032 mol, example 421, step 1) in methanol (1.0 mL, 0.025 mol) followed by sodium triacetoxyborohydride (0.20 g, 0.00095 mol), and the mixture was stirred for 1 h. The crude product was purified by prep-HPLC. LC-MS: 432.3 (M+H)+

Workup

customThe crude product was purified by prep-HPLC

Sources & evidence

ORD record: ord-0d24fbf711994a88ac524e14dfada7a8
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08058288B2

Reaction notes

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