Camptothecin → HCID 4442037, compound

HRID 427426Notes

Reaction equation

[BH4-].[Na+].[CH3:3][CH2:4][C@@:5]1([OH:28])[C:10](=[O:11])[O:9][CH2:8][C:7]2[C:12]([N:14]3[C:26](=[CH:27][C:6]1=2)[C:25]1[C:16](=[CH:17][C:18]2[C:23]([N:24]=1)=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:15]3)=[O:13]>CO>[CH2:4]([C:5]1([OH:28])[C:6]2[CH:27]=[C:26]3[N:14]([CH2:15][C:16]4[C:25]3=[N:24][C:23]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[CH:17]=4)[C:12](=[O:13])[C:7]=2[CH2:8][O:9][CH:10]1[OH:11])[CH3:3]

Participants

Conditions

Temperature: 55 °C

Procedure

Sodium borohydride (14 g, 370 mmol) is added in portions to a suspension of (S)-(+)-camptothecin (14 g, 40 mmol, that may be obtained using different commercial sources such as Aldrich Chemical Co. (Milwaukee, Wis.)), in methanol (750 ml) and the resulting mixture is heated slowly to 55° C. so as to obtain a clear solution that is then agitated for 16 hours at ambient temperature. The solvent is then evaporated under reduced pressure, the residue is recovered in water (250 ml), neutralized by the addition of acetic acid (21 ml) and left alone for 2 hours at 4° C. The resulting suspension is filtered and washed successively with cold water, acetone and diethyl ether, which, after drying under reduced pressure, permits obtaining the sought compound in the form of a white solid, m.p. 280° C.

Workup

customto obtain a clear solution that
customThe solvent is then evaporated under reduced pressure
customthe residue is recovered in water (250 ml)
additionneutralized by the addition of acetic acid (21 ml)
waitleft alone for 2 hours at 4° C
filtrationThe resulting suspension is filtered
washwashed successively with cold water, acetone and diethyl ether, which
customafter drying under reduced pressure
custompermits obtaining the sought compound in the form of a white solid, m.p. 280° C.

Sources & evidence

ORD record: ord-ce4b67517d994bbaaca9db15b427dcf5
Source dataset: uspto-grants-2001_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06313135B1

Reaction notes

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