Ammonia → HCID 12962022, compound

HRID 1065710Notes

Reaction equation

HRID 1065710 reaction equation
C(O)(=O)C.C(O)(=O)C.OC1C=CC2[C@@H]3[C@H]([C@H]4[C@@](CC3)(C)C(=O)[C@H](O)C4)CCC=2C=1.N.[BH4-].[Na+].[NH2:33][C@H:34]1[C@H:39]([OH:40])[CH2:38][C@H:37]2[C@H:41]3[C@H:50]([CH2:51][CH2:52][C@:35]12[CH3:36])[C:49]1[CH:48]=[CH:47][C:46]([OH:53])=[CH:45][C:44]=1[CH2:43][CH2:42]3.[C:54]([OH:66])(=[O:65])[CH2:55][C:56]([CH2:61][C:62]([OH:64])=[O:63])([C:58]([OH:60])=[O:59])[OH:57]>C(O)C.CS(C)=O>[C:54]([OH:66])(=[O:65])[CH2:55][C:56]([CH2:61][C:62]([OH:64])=[O:63])([C:58]([OH:60])=[O:59])[OH:57].[NH2:33][C@H:34]1[C@H:39]([OH:40])[CH2:38][C@H:37]2[C@H:41]3[C@H:50]([CH2:51][CH2:52][C@:35]12[CH3:36])[C:49]1[CH:48]=[CH:47][C:46]([OH:53])=[CH:45][C:44]=1[CH2:43][CH2:42]3

Participants

8

Reactant 5

HCID 222AmmoniaHCID 311Citric AcidHCID 4311764Sodium borohydrideHCID 12962023HCID 12962023, compoundHCID 86738380HCID 86738380, compound

Product 1

HCID 12962022HCID 12962022, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 702EthanolSolvent

Procedure

In a similar way as described in Example XIII 3,16α-dihydroxy-oestra-1,3,5(10)-trien-17-one diacetate was converted with a saturated solution of ammonia in ethanol and in the presence of a type 3 A molecular sieve, followed by sodium borohydride reduction of the intermediate 17-imine, into 17β-amino-oestra-1,3,5(10)-triene-3,16α-diol. Reaction of the latter compound with citric acid gave 17β-amino-oestra-1,3,5(10)-triene-3,16α-diol citrate (1:1) (salt), m.p. >220° C. (decomp.), [α]D +24° (c 0.9 in dimethylsulphoxide).

Sources & evidence

ORD record
ord-52a7e8a2dd6a44b2a7dc1c8f3fae88d7
Source dataset
uspto-grants-1982_05
Patent number
US04330539

Reaction notes

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